Rapid Microwave-Assisted Solid Phase Peptide Synthesis
|
|
- Adelia Parrish
- 8 years ago
- Views:
Transcription
1 592 SPECIAL TOPIC Rapid Microwave-Assisted Solid Phase Peptide Synthesis Rapid Máté Microwave-Assisted Solid Phase Peptide SynthesisErdélyi, a,b Adolf Gogoll* a a Department of Organic Chemistry, Uppsala University, Box 53, 75 2 Uppsala, Sweden Fax +46(8)52524; mate@kemi.uu.se, adolf@kemi.uu.se b Department of Medicinal Chemistry, Uppsala University, Box 574, Uppsala, Sweden Fax +46(8) Received 20 May 2002 Dedicated to Prof. Hans-J. Schäfer on the occasion of his 65 th birthday Abstract: A microwave-assisted, rapid solid phase peptide synthesis procedure is presented. It has been applied to the coupling of sterically hindered Fmoc-protected amino acids yielding di- and tripeptides. Optimized conditions for a variety of coupling reagents are reported. Peptides were obtained rapidly (.5 20 min) and without racemization. Key words: SPPS, microwave, amino acids, peptide coupling, solid-phase Since Merrifield s pioneering work on solid phase peptide synthesis (SPPS), peptide preparation has almost exclusively been performed on resin. The generation of combinatorial libraries has caused a renaissance and growth of interest in solid supported chemistry. Parallel to the developments in combinatorial chemistry, it has been shown that the use of microwave heating can be advantageous in a large variety of organic reactions. 2 However, there have been only very few reports on the use of microwave heating in combination with solid phase synthesis, 3 possibly due to the requirement of special heavy-walled vials for microwave irradiation that makes resin handling rather complicated, and problems to control reaction conditions. In particular, enhancement of SPPS by the use of microwave heating has so far received little attention. Peptide synthesis performed in a kitchen microwave oven was published in However, the procedure described by Wang et al is not easily reproducible, because of the use of a commercial microwave oven for irradiation, and the lack of temperature control. The couplings were made using symmetric amino acid anhydrides or pre-formed N- hydroxybenzotriazole activated esters, yielding 2 4 fold reaction rate enhancements. In general, peptide chemistry is today limited to room temperature conditions, originating from the general belief of the heat-sensitivity of peptide coupling reagents (Table). Here, we describe a microwave-enhanced, rapid (.5 20 min) procedure for the coupling of sterically hindered amino acids on solid phase. The optimized conditions for a variety of common coupling reagents yielded a significant rate increase. Single mode irradiation with monitoring of temperature, pressure and irradiation power versus Synthesis 2002, No., Print: Art Id X,E;2002,0,,592,596,ftx,en;C0802SS.pdf. Georg Thieme Verlag Stuttgart New York ISSN Table Coupling Times and Temperatures for Peptide Synthesis on Rink s Amide Resin Employing a Variety of Coupling Reagents a Coupling Reagent PyBOP Mukaiyama s Reagent TBTU HATU Reaction time (min) Temperature ( C) Solvent DMF CH 2 Cl 2 DMF DMF a The average pressure for reactions performed in DMF and CH 2 Cl 2 was 2 bar and 6 8 bar, respectively. time was used throughout, making the procedure highly reproducible. Our goal was to investigate the compatibility of HATU, 5a TBTU, 5b PyBOP 5c and Mukaiyama s reagent 5d mediated couplings at high temperatures. Reaction conditions for the synthesis of a small tripeptide containing the three most hindered natural amino acids (Fmo-Thr-Val-Ile- NH 2 ), and the Fmoc-Ala-Ile-NH 2 or Fmoc-Thr-Ile-NH 2 dipeptides were optimized. The coupling of Fmoc-protected amino acids on polystyrene resin using Rink amide linker was performed. No degradation of the solid support was observed. Fast Fmoc-deprotection steps (5 minutes) were conducted at room temperature, and the coupling steps were performed using microwave irradiation. All coupling steps were monitored by qualitative ninhydrin test 6 and by LC-MS investigation of peptides cleaved from small amounts of the resin. Our optimized conditions are shown in the Table. The azobenzotriazole derivatives have shown an increased coupling efficiency with increasing temperature up to 0 C. At higher temperatures the decomposition of the reagents was indicated by the colour change of the reaction mixtures. In contrast with the usual SPPS procedures where double or triple coupling steps are needed for completion, under microwave conditions, coupling was complete already in a few minutes after a single coupling step. The absence of racemization during the high temperature treatment of amino acids in the presence of a base (i- Pr 2 NEt) was investigated by LC-MS and H NMR. The presence of only one peak in the chromatogram (Figure ) of the synthesized peptides suggested the absence of dias-
2 SPECIAL TOPIC Rapid Microwave-Assisted Solid Phase Peptide Synthesis 593 Figure The LC-MS chromatogram of Fmoc-Ala-Ile-NH 2 prepared by PyBOP mediated couplings at 0 C. tereomeric compounds. The H NMR spectrum of this material containing a single set of signals of the oligopeptide suggested the presence of only one diastereomer. As an example, the aliphatic region of the H NMR spectrum of a synthesized dipeptide is shown in Figure 2. The efficiency of the solid phase methodology was limited by the need of transfer between different reaction vessels to perform the coupling and washing steps. The high pressure generated by volatile components during reactions carried out with microwave irradiation makes the use of special heavy-walled vials highly recommendable. However, these vials are not suitable for filtration. Therefore, the reaction mixtures were transferred for washing and deprotection steps into plastic columns equipped with a polypropylene frit, causing some loss of resin. Moderate yields could therefore be obtained for the synthesis of the di- (PyBOP: 60%; Mukaiyama s reagent: 35%; TBTU: 4%; HATU 24%) and tripeptides (PyBOP: 48%; Mu- Figure 2 The aliphatic region of the H NMR spectrum of Fmoc-Ala-Ile-NH 2 showing the presence of one diastereomer after microwave assisted synthesis (PyBOP mediated couplings at 0 C).
3 594 M. Erdélyi, A. Gogoll SPECIAL TOPIC kaiyama s reagent: 65%; TBTU: 3%; HATU 42%). The efficiency of the solid phase methodology including the loading (PyBOP, i-pr 2 NEt, DMF, 0 C), cleavage (95% TFA in CH 2 Cl 2 ) and purification (preparative LC-MS) steps was determined by attachment and cleavage of a single Fmoc-Ile to the resin, yielding 60% of the expected product. The efficiency of the methodology might be increased by instrumental improvements, e.g., by the development of heavy-walled vials more compatible with the handling of resins used in solid phase synthesis. This synthetic method will be of considerable interest for incorporation of sterically hindered and deactivated nonnatural amino acids in peptide synthesis on solid phase. All reactions were conducted in heavy-walled glass Smith Process Vials sealed with aluminum crimp caps fitted with a silicon septum. The inner diameter of the vial filled to the height of 3.5 cm was.3 cm. The microwave heating was performed in a Smith Synthesizer single mode microwave cavity producing continuous irradiation at 2450 MHz (Personal Chemistry AB, Uppsala, Sweden). Reaction mixtures were stirred with a magnetic stir bar during the irradiation. The temperature, pressure and irradiation power were monitored during the course of the reaction. The average pressure during the reaction run in DMF was -2 bar, for the reactions run in CH 2 Cl 2 it was 6 8 bar. After completed irradiation, the reaction tube was cooled with high-pressure air until the temperature had fallen below 39 C (ca. 2 min). H NMR spectra were recorded for CD 3 CN solutions at 400 MHz (Jeol JNM EX400 spectrometer) at r.t. Chemical shifts are referenced indirectly to TMS via the residual solvent signal (d =2.0). The H NMR spectra of all synthesized compounds have been fully assigned using data from phase-sensitive DQF- COSY 7 and NOESY 8 experiments. The ESI-MS spectra of the peptides were obtained with a Finnigan ThermoQuest AQA mass spectrometer (ESI 30eV, probe temperature 00 C) equipped with a Gilson 322-H2 GradientPump system, an SB-C8 analytical and an SB-C8 (5 mm, 2.2 mm, 50 mm) preparative column. A H 2 O MeCN formic acid (0.05%) mobile phase was used with a gradient of 20%-80% MeCN during 7 minutes on the analytical column, and minutes on the preparative column. The starting materials were purchased from commercial suppliers and were used without purification with the exception of CH 2 Cl 2 which was freshly distilled over calcium hydride. Fmoc-Ala, Fmoc- Ile, Fmoc-Val, PyBOP, and Rink amide MBHA resin were obtained from Novabiochem, Fmoc-Thr(t-Bu)-OH from Alexis Biochemicals (USA). TBTU was from Richelieu Biotechnologies (Canada). HATU was purchased from PE Biosystems (United Kingdom). Trifluoroacetic acid (99%), N,N-diisopropylethylamine (redistilled 99.5%), and piperidine (99%) were from Aldrich (Germany). DMF was obtained from Fluka (Denmark). Fmoc-Thr-Val-Ile-NH 2 (); Method A Procedure I Rink amide resin (300 mg, 0.78 mmol/g, mmol) was treated with 20% piperidine in DMF (5 ml for 0 and 5 minutes) in a column equipped with polypropylene frit placed in an overhead mixer. The soln was then drained, and the resin was washed with DMF (3 5 ml) and CH 2 Cl 2 (3 5 ml). Procedure II The resin from procedure I was transferred into a Smith Process Vial and Fmoc-Ile (248 mg, 0.70 mmol), PyBOP (343 mg, 0.70 mmol), i-pr 2 NEt (0.25 ml,.40 mmol) and DMF (3 ml) was added. The mixture was irradiated in a microwave cavity at 0 C for 20 min. Then, the mixture was transferred into a column equipped with a polypropylene frit using a Pasteur pipette. The soln was drained and the resin was washed with DMF (3 5 ml) and CH 2 Cl 2 (3 5 ml). The completion of the coupling was confirmed by Kaisers test. Thereafter, Fmoc-deprotection was performed using procedure I as described above. Procedure III The resin from procedure I was transferred into a Smith Process Vial and Fmoc-Val (238 mg, 0.70 mmol), PyBOP (343 mg, 0.70 mmol), i-pr 2 NEt (0.25 ml,.40 mmol) and DMF (3 ml) was added. The coupling was performed using procedure II as described above. The completion of the coupling was confirmed by Kaisers test and by cleavage of a small amount of the resin with 95% TFA in CH 2 Cl 2 and analytical LC-MS investigation of the cleaved peptide. Thereafter, Fmoc-deprotection was performed using procedure I as described above. The resin was transferred into a Smith Process Vial and Fmoc- Thr(t-Bu) (279 mg, 0.70 mmol), PyBOP (343 mg, 0.70 mmol), i- Pr 2 NEt (0.23 ml,.32 mmol) and DMF (3 ml) was added. The mixture was irradiated using procedure II, the completion of reaction was confirmed by procedure III. Procedure IV Finally, the tripeptide was cleaved from the resin using 95% TFA in CH 2 Cl 2 (2 hours). The soln was separated from the resin by filtration, the resin was washed with additional CH 2 Cl 2 (5 ml) and the combined phases were concentrated on a rotatory evaporator. The residue was then dissolved in MeCN ( 2 ml) and was purified on preparative LC-MS yielding as a white solid (63 mg, 0. mmol, 48%). Method B Rink amide resin (300 mg, 0.78 mmol/g, mmol) was deprotected Vial and Fmoc-Ile (248 mg, 0.70 mmol), 2-fluoro--methylpyridinium tosylate (20 mg, 0.70 mmol), i-pr 2 NEt (0.25 ml,.40 mmol) and DMF (3 ml) was added and the subsequent synthesis steps followed the procedure described for Method A, with the exception of the coupling times and temperature (0 minutes at 30 C), yielding as a white solid (83 mg, 0.5 mmol, 65%). Method C Rink amide resin (300 mg, 0.78 mmol/g, mmol) was deprotected Vial and Fmoc-Ile (248 mg, 0.70 mmol), TBTU (225 mg, 0.70 mmol), i-pr 2 NEt (0.25 ml,.40 mmol) and DMF (3 ml) was added and the subsequent synthesis steps followed the procedure described for Method A, with exception of the coupling times (0 minutes at 0 C), yielding as a white solid (4 mg, mmol, 3%). Method D Rink amide resin (30 mg, 0.73 mmol/g, mmol) was deprotected Vial and Fmoc-Ile (233 mg, 0.66 mmol), HATU (56 mg, 0.66 mmol), i-pr 2 NEt (0.23 ml,.32 mmol), DMF (3 ml) was added and the subsequent synthesis steps followed the procedure described for Method A, with exception of the coupling times (.5 min. at 0 C), yielding as a white solid (29 mg, mmol, 42%). H NMR (400 MHz, CD 3 CN): d = 7.83 (d, J = 7.2 Hz, 2 H, Fmoc), 6.67 (br d, J = 7.6 Hz, 2 H, Fmoc), 7.42 (ddd, J =.2, 7.6, 7.6 Hz, 2 H, Fmoc), 7.34 (ddd, J =.2, 7.2, 7.6 Hz, 2 H, Fmoc), 7.5 (br d, H, NH-Val), 6.80 (br d, H, NH-Ile), 6.35 (br s, H, NH), 6.08 (br d, H, NH-Thr), 5.79 (br s, H, NH), 4.33 (dd, J = 5.9, 7.3 Hz, H, CH a -Val), 4.3 (d, J = 6.6 Hz, 2 H, CH 2 -Fmoc), 4.24 (t, J =6.6
4 SPECIAL TOPIC Rapid Microwave-Assisted Solid Phase Peptide Synthesis 595 Hz, H, CH-Fmoc), 4.7 (dd, J = 6.8 Hz, H, CH a -Ile), (m, 2 H, CH b -Thr, CH a -Thr),.7.8 (m, 2 H, CH b -Val, CH b -Ile),.44 (m, H, CH 2g(a)-Ile),.26 (d, J =Hz, 3 H, CH 3 -Thr),.0 (m, H, CH 2g(b)-Ile), (m, 2 H, CH 3g -Ile, CH 3d -Ile, CH 3g -Val). ESI-MS: m/z = 553 (M + ) +, 536, 522, 423, 79. Fmoc-Ala-Ile-NH 2 (2); Method A2 Rink amide resin (300 mg, 0.73 mmol/g, mmol) was deprotected Smith Process Vial and Fmoc-Ile (233 mg, 0.66 mmol), PyBOP (343 mg, 0.70 mmol), i-pr 2 NEt (0.23 ml,.32 mmol), DMF (3 ml) was added and the loading of resin was made following procedure II (0 C, 5 min), the confirmation of the completion of the reaction was made following procedure III. Fmoc-deprotection (procedure I) was followed by the coupling of Fmoc-Ala (205 mg, 0.66 mmol) in the presence of PyBOP (343 mg, 0.70 mmol), i-pr 2 NEt (0.23 ml,.32 mmol) and DMF (3 ml) following procedure III (0 C, 5 min). This step was repeated due to the incomplete coupling observed by the Kaisers test. The resin was washed with portions of DMF (3 5 ml), portions of CH 2 Cl 2 (3 5 ml) and the dipeptide was cleaved following procedure IV yielding 2 as a white solid (56 mg, 0.32 mmol, 60%). Method B2 Rink amide resin (30 mg, 0.78 mmol/g, mmol) was deprotected Vial and Fmoc-Ile (233 mg, 0.66 mmol), 2-fluoro--methylpyridinium tosylate (20 mg, 0.70 mmol), i-pr 2 NEt (0.23 ml,.32 mmol), DMF (3 ml) was added and the subsequent steps were made following Method A2 with the exception of the reaction times and temperature (0 C, 0 min) yielding 2 as a white solid (35 mg, mmol, 35%). Method C2 Rink amide resin (299 mg, 0.78 mmol/g, mmol) was deprotected Smith Process Vial and Fmoc-Ile (233mg, 0.66 mmol), TBTU (225 mg, 0.70 mmol), i-pr 2 NEt (0.23 ml,.32 mmol) and DMF (3 ml) was added and the subsequent steps were made following Method A2 with the exception of the reaction times and temperature (0 C, 0 min) yielding 2 as a white solid (4 mg, mmol, 4%). H NMR (400 MHz, CD 3 CN): d = 7.83 (d, J = 7.7 Hz, 2 H, Fmoc), 7.67 (br d, J = 7.3 Hz, 2 H, Fmoc), 7.42 (ddd, J =.2, 7.7, 7.7 Hz, 2 H, Fmoc), 7.33 (ddd, J =.2, 7.3, 7.7 Hz, 2 H, Fmoc), 6.78 (br d, J = 7.7 Hz, H, NH-Ile), 6.34 (br s, H, NH), 6.08 (br d, J =5.9 Hz, H, NH-Ala), 5.75 (br s, H, NH), 4.32 (d, J = 7.0 Hz, 2 H, CH 2 -Fmoc), 4.24 (t, J = 7.0 Hz, H, CH-Fmoc), 4.6 (dd, J =5.8, 8.0 Hz, H, CH a -Ile), 4.09 (dq, J = 5.9, 7.0 Hz, H, CH a -Ala),.77 (m, H, CH b -Ile),.42 (m, H, CH 2g(a)-Ile),.39 (d, J =7.0 Hz, 3 H, CH 3 -Ala),.09 (m, H, CH 2g(b)-Ile), 0.87 (d, J = 6.8 Hz, 3 H, CH 3g -Ile), 0.84 (t, J = 7.4 Hz, 3 H, CH 3d ESI-MS: m/z = 424 (M + ) +, 407, 379, 79. Fmoc-Thr-Ile-NH 2 (3); Method D3 Rink s amide resin (300 mg, 0.78 mmol/g, mmol) was deprotected Smith Process Vial and Fmoc-Ile (248 mg, 0.70 mmol), HATU (66 mg, 0.70 mmol), i-pr 2 NEt (0.25 ml,.40 mmol), DMF (3 ml) was added and the loading of the resin was made following procedure II (0 C,.5 min), the confirmation of the completion of the reaction was made following procedure III. Fmoc-deprotection (procedure I) was followed by the coupling of Fmoc-Thr(t-Bu) (279 mg, 0.70 mmol) in the presence of HATU (343 mg, 0.70 mmol), i- Pr 2 NEt (0.23 ml,.32 mmol) and DMF (3 ml) following procedure III (0 C,.5 min). The resin was washed with portions of DMF (3 5 ml), portions of CH 2 Cl 2 (3 5 ml) and the dipeptide was cleaved following procedure IV yielding 3 as a white solid (25.4 mg, 0.06 mmol, 24%). H NMR (400 MHz, CD 3 CN): d = 7.83 (d, J = 7.5 Hz, 2 H, Fmoc), 7.68 (br d, J = 7.0 Hz, 2 H, Fmoc), 7.42 (ddd, J =.2, 7.5, 7.5 Hz, 2 H, Fmoc), 7.33 (ddd, J =.2, 7.0, 7.5 Hz, 2 H, Fmoc), 6.87 (br d, J = 8.4 Hz, H, NH-Ile), 6.44 (br s, H, NH), 5.99 (br d, J =5.9 Hz, H, NH-Thr), 5.85 (br s, H, NH), 4.36 (d, J = 7.5 Hz, 2 H, CH 2 -Fmoc), 4.25 (t, J = 7.5 Hz, H, CH-Fmoc), 4.22 (dd, J =5.9, 8.4 Hz, CH a -Ile), (m, 2 H, CH b -Thr, CH a -Thr),.83 (m, H, CH b -Ile),.45 (m, H, CH 2g(a)-Ile),.4 (m, H, CH 2g(b)-Ile),.08 (d, J = 6.0 Hz, 3 H, CH 3g -Thr), 0.90 (d, J = 7.0 Hz, 3 H, CH 3g - Ile), 0.87 (t, J = 7.7 Hz, 3 H, CH 3d ESI-MS: m/z = 454 (M + ) +, 437, 409, 255, 24, 99. Efficiency of the Solid Phase Methodology Rink amide resin (297 mg, 0.78 mmol/g, mmol) was deprotected using procedure I. The resin was then transferred into a Smith Process Vial, Fmoc-Ile (25 mg, 0.70 mmol), PyBOP (343 mg, 0.70 mmol), i-pr 2 NEt (0.25 ml,.40 mmol), and DMF (3 ml) was added. The mixture was irradiated in a microwave cavity at 0 C for 5 minutes. Then, the mixture was transferred into a column equipped with a polypropylene frit and was washed following procedure II. The completion of the coupling was confirmed by Kaisers test. The resin was cleaved and purified following procedure IV yielding Fmoc-Ile-NH 2 as a white solid (49 mg, 0.4 mmol, 60%). H NMR (400 MHz, CDCl 3 ) d = 7.76 (d, J = 7.5 Hz, 2 H, Fmoc), 7.57 (br d, J = 7.3 Hz, 2 H, Fmoc), 7.40 (dd, J = 7.3, 7.3 Hz, 2 H, Fmoc), 7.3 (dd, J = 7.3, 7.5 Hz, 2 H, Fmoc), 5.89 (br s, H, NH), 5.66 (br s, H, NH), 5.36 (br d, J = 8.4 Hz, H, NH-Ile), 4.42 (d, J = 6.7 Hz, 2 H, Fmoc-CH 2 ), 4.20 (t, J = 6.7 Hz, H, CH-Fmoc), 4.07 (dd, J = 8.4, 8.4 Hz, H, CH a -Ile),.89 (m, H, CH b -Ile),.52 (m, H, CH g(a)-ile),.3 (m, H, CH g(b)-ile), (m, 6 H, CH 3g-Ile, CH 3d ESI-MS: m/z = 353 (M+) +. Acknowledgements We would like to thank Personal Chemistry AB for access to the Smith Synthesizer TM and Uppsala University for financial support. References () Merrifield, R. B. J. Am. Chem. Soc. 963, 85, 249. (2) Lindström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 200, 57, (3) (a) Stadler, A.; Kappe, C. O. Eur. J. Org. Chem. 200, 99. (b) Kuster, G.; Scheren, H. W. Tetrahedron Lett. 2000, 4, 55. (c) Hoel, A. M. L.; Nielsen, J. Tetrahedron Lett. 999, 40, 394. (d) Larhed, M.; Lindeberg, G.; Hallberg, A. Tetrahedron Lett. 996, 37, 829. (e) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95. (4) (a) Chen, S.-T.; Chiou, S.-H.; Wang, K.-T. J. Chin. Chem. Soc. 99, 38, 85. (b) Yu, H.-M.; Chen, S.-T.; Wang, K.-T. J. Org. Chem. 992, 57, 478. (c) Chen, S.-T.; Tseng, P.-H.; Yu, H.-M.; Wu, C.-Y.; Hsiao, K.-F.; Wu, S.-H.; Wang, K.- T. J. Chin. Chem. Soc. 997, 44, 69. (5) (a) HATU: O-(7-Azabenzotriazol--yl)-N,N,N,N tetramethyluronium hexafluoro-phosphate see: Carpino, L. A.; El-Faham, A.; Minor, C. A.; Albericio, F. J. Chem. Soc., Chem Commun. 994, 20. (b) TBTU: O-(Azabenzotriazol- -yl)-n,n,n,n -tetramethyluronium tetrafluoro-borate see: Zimmer, S.; Hoffmann, E.; Jung, G.; Kessler, H. Liebigs Ann. Chem. 993, 5, 497. (c) PyBOP: (Benzotriazol-- yloxy)-tripyrrolidinophosphonium hexa-fluorophosphate
5 596 M. Erdélyi, A. Gogoll SPECIAL TOPIC see: Coste, J.; Le-Nguyen, D.; Castro, B. Tetrahedron Lett. 990, 3, 205. (d) Mukaiyama s reagent: 2-fluoro-- methyl-pyridinium tosylate see: Mukaiyama, T.; Tanaka, T. Chem. Lett. 976, 303. (6) Sarin, V. K.; Kent, S. B.; Tam, J. P.; Merrifield, R. B. Anal. Biochem. 98, 7, 47. (7) (a) Wokaun, A.; Ernst, R. R. Chem. Phys. Lett. 977, 52, 407. (b) Shaka, A. J.; Freeman, R. J. Magn. Reson. 983, 5, 69. (8) (a) Kumar, A.; Ernst, R. R.; Wüthrich, K. Biochem. Biophys. Res. Commun. 980, 95,. (b) Bodenhausen, G.; Kogler, H.; Ernst, R. R. J. Magn. Res. 984, 58, 370.
Novel Method for Solid Phase Peptide Synthesis Using Microwave Energy
Novel Method for Solid Phase Peptide Synthesis Using Microwave Energy Jonathan M. Collins, Michael J. Collins, Rebecca C. Steorts CEM Corporation, Matthews, NC 28106-0200, U.S.A. Presented at American
More informationExperimental procedures. Solid phase peptide synthesis (SPPS)
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 214 Experimental procedures Solid phase peptide synthesis (SPPS) Solid phase
More information1) Technical informations. - a) How does it work? - b) Purification - c) Quality Control. 2) Standard synthesis
1) Technical informations - a) How does it work? - b) Purification - c) Quality Control 2) Standard synthesis - a) Standard peptides - b) Modified peptides - c) Shipment and Delivery Time - d) How to order?
More informationPeptide Synthesis Zheng Miao* and Zhen Cheng
Peptide Synthesis Zheng Miao* and Zhen Cheng 1 Department of Radiology, Molecular Imaging Program at Stanford, Stanford University School of Medicine, Stanford, USA *For correspondence: zmiao@stanford.edu
More informationSmall μmol Scale Synthesis of a Labeled Antimicrobial Peptide using Biotage
Application ote A098 Small μmol Scale Synthesis of a Labeled Antimicrobial Peptide Page 1 Small μmol Scale Synthesis of a Labeled Antimicrobial Peptide using Biotage Initiator+ Alstra Introduction Labeled
More information1. COUPLING REAGENTS : Structure and acronyms
Coupling Reagents 1. COUPLING REAGENTS : Structure and acronyms... 2 2. CARBODIIMIDE... 3 1.a. N,N -Dicyclohexylcarbodimide (DCC)... 3 DCC/HOBt coupling experimental procedure:... 4 1.b. N-(3-Dimethylaminopropyl)-N
More informationSupporting Information
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2013 More than Meets the Eye: Conformational Switching of a Stacked Dialkoxynaphthalene Naphthalenetetracarboxylic diimide
More informationShort Peptide Synthesis
Short Peptide Synthesis Keith ó Proinsias 8 th February 2010 Introduction Amide bond and basic amide synthesis Solution phase peptide synthesis Protecting groups required for peptide synthesis Coupling
More informationThe latest SPPS application data
The latest SPPS application data -innovative solution for peptide chemistry- Biotage Japan Ltd. Fumio Kumakura Ph,D Biotage With more than 5,000 discovery chemistry systems installed in over 600 facilities
More informationOverview'of'Solid-Phase'Peptide'Synthesis'(SPPS)'and'Secondary'Structure'Determination'by'FTIR'
verviewofsolid-phasepeptidesynthesis(spps)andsecondarystructuredeterminationbyftir Introduction Proteinsareubiquitousinlivingorganismsandcells,andcanserveavarietyoffunctions.Proteinscanactas enzymes,hormones,antibiotics,receptors,orserveasstructuralsupportsintissuessuchasmuscle,hair,and
More informationInvestigation of Solid-Phase Peptide Synthesis by the Near-Infrared Multispectral Imaging Technique: A Detection Method for Combinatorial Chemistry
Anal. Chem. 1999, 71, 2255-2261 Accelerated Articles Investigation of Solid-Phase Peptide Synthesis by the Near-Infrared Multispectral Imaging Technique: A Detection Method for Combinatorial Chemistry
More informationStructure-Based Design of Covalent Siah Inhibitors
Chemistry & Biology, Volume 20 Supplemental Information Structure-Based Design of Covalent Siah Inhibitors John L. Stebbins, Eugenio Santelli, Yongmei Feng, Surya K. De, Angela Purves, Khatereh Motamedchaboki,
More informationFocus XC. Ultimate Fully Automated Peptide Synthesizer with Sonication and Heating Options
Focus XC Ultimate Fully Automated Peptide Synthesizer with Sonication and Heating Options FOCUS XC AUTOMATED PEPTIDE SYNTHESIZER aapptec s Focus XC is a compact, easy to use fully automated peptide synthesizer
More informationSpatial Screening of Cyclic Neoglycopeptides: Identification of Multivalent Wheat Germ Agglutinin Ligands**
1 Spatial Screening of Cyclic Neoglycopeptides: Identification of Multivalent Wheat Germ Agglutinin Ligands** Valentin Wittmann* and Sonja Seeberger Experimental Section General. Solid-phase peptide synthesis
More informationSolid-Phase Peptide Synthesis using N α -Trityl-Amino Acids. Jordi Girona 18-26, E-08034 Barcelona, Spain. planta, E-08028 Barcelona, Spain.
Solid-phase peptide synthesis using N α -trityl-amino acids. de la Torre, B.G., Marcos, M.A., Eritja, R., Albericio, F. Letters in Peptide Sience 8, 331-338 (2002). Solid-Phase Peptide Synthesis using
More informationSolid-phase Synthesis of Homodimeric Peptides: Preparation of Covalently-linked Dimers of Amyloid-beta Peptide
Electronic Supplementary Information Solid-phase Synthesis of Homodimeric Peptides: Preparation of Covalently-linked Dimers of Amyloid-beta Peptide W. Mei Kok, a,b,c Denis B. Scanlon, b John A. Karas,
More informationAutomated Fast-Bead Synthesis of Small Peptides
Automated Fast-Bead Synthesis of Small Peptides Application Note 228 Joan Stevens, Ph.D., Norbert Wodke, Tim Hegeman and Kirby Reed (Gilson, Inc.) Introduction In proteomic research, the synthesis of peptides
More informationMicrowave irradiated high-speed solution synthesis of peptide acids employing Fmoc-amino acid pentafluorophenyl esters as coupling agents
Indian Journal of Chemistry Vol. 44B, ovember 2005, pp. 2328-2332 Microwave irradiated high-speed solution synthesis of peptide acids employing Fmoc-amino acid pentafluorophenyl esters as coupling agents
More informationRapid solid-phase peptide synthesis using thermal and controlled microwave irradiation
Journal of Peptide Science Published online in Wiley InterScience (www.interscience.wiley.com)..771 Rapid solid-phase peptide synthesis using thermal and controlled microwave irradiation BERNADETT BACSA,
More informationStructural basis for the enhanced activity of cyclic antimicrobial peptides: the case of BPC194
SUPPLEMENTARY DATA Structural basis for the enhanced activity of cyclic antimicrobial peptides: the case of BPC194 Jacek T. Mika,a, Gemma Moiset,a, Anna D. Cirac a,b, Lidia Feliu c, Eduard Bardají c, Marta
More informationFAST AND EFFICIENT PURIFICATION OF SYNTHETIC PEPTIDES BY SOLID-PHASE EXTRACTION
ACTA CHROMATOGRAPHICA, NO. 14, 2004 FAST AND EFFICIENT PURIFICATION OF SYNTHETIC PEPTIDES BY SOLID-PHASE EXTRACTION W. Kamysz 1,*, M. Okrój 2, E. Łempicka 3, T. Ossowski 3, and J. Łukasiak 1 1 Faculty
More informationSynthesis of hydrophilic and flexible linkers for peptide derivatization in solid phase
Bioorganic & Medicinal Chemistry Letters 14 (2004) 161 165 Synthesis of hydrophilic and flexible linkers for peptide derivatization in solid phase Aimin Song, a Xiaobing Wang, a Jinhua Zhang, b Jan Marˇ
More informationPeptides: Synthesis and Biological Interest
Peptides: Synthesis and Biological Interest Therapeutic Agents Therapeutic peptides approved by the FDA (2009-2011) 3 Proteins Biopolymers of α-amino acids. Amino acids are joined by peptide bond. They
More informationHow To Make A Peptide
A two-step fluorous capping procedure in solid phase peptide synthesis CHAPTER 5 Introduction: The synthesis of peptides by solid phase procedures has reached a high level of efficiency and oligopeptides
More informationSupplementary Information. Primary amino acid lithium salt as a catalyst for asymmetric Michael addition of isobutyraldehyde with β-nitroalkenes.
This journal is (c) The Royal Society of Chemistry 8 Supplementary Information Primary amino acid lithium salt as a catalyst for asymmetric Michael addition of isobutyraldehyde with β-nitroalkenes. Atsushi
More informationStandard practices for Fmoc-based solid-phase. peptide synthesis in the Nowick laboratory. (Version 1.6.1)
Standard practices for Fmoc-based solid-phase peptide synthesis in the Nowick laboratory (Version 1.6.1) Adam G. Kreutzer and Patrick J. Salveson E-mail: Contents Contributions to this guide 3 General
More informationUSP's Therapeutic Peptides Expert Panel discusses manufacturing processes and impurity control for synthetic peptide APIs.
Control Strategies for Synthetic Therapeutic Peptide APIs Part III: Manufacturing Process Considerations By Brian Gregg,Aleksander Swietlow,Anita Y. Szajek,Harold Rode,Michael Verlander,Ivo Eggen USP's
More informationCoupling Reagents. Carbodiimides
Coupling Reagents Carbodiimides Dicyclohexylcarbodiimide (DCC) and diisopropylcarbodiimide (DIC) are commonly used to prepare amides, esters and acid anhydrides from carboxylic acids. These reagents can
More informationSupplemental data. A simple and effective cleavable linker for chemical proteomics applications
Supplemental data A simple and effective cleavable linker for chemical proteomics applications Yinliang Yang, annes ahne, Bernhard Kuster, and Steven. L. Verhelst * Figure S1 Figure S2 Figure S3 Table
More informationSolid Phase Peptide Synthesis Methodology with Integrin α5 and Ligand Ac-RGDNP-NH2
Solid Phase Peptide Synthesis Methodology with Integrin α5 and Ligand Ac-RGDNP-NH2 Amy Ho The University of Texas at Dallas 2006 Abstract Peptides are short chains of amino acids that biologically function
More informationPeptide Library Synthesis
Peptide Library Synthesis Jamie M. R. Moore Guy Laboratory UCSF I. verview.. page 2 II. Reagents and Apparatus. page 4 III. Flow Chart. page 6 IV. Protocol. page 7 IV. Tables A. List of Fmoc Amino. page
More informationA prochelator with a modular masking group featuring hydrogen peroxide activation with concurrent fluorescent reporting
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information A prochelator with a modular masking group featuring hydrogen peroxide activation
More informationHow To Make A Peptide
Peptide synthesis From Wikipedia, the free encyclopedia In organic chemistry, peptide synthesis is the creation of peptides, which are organic compounds in which multiple amino acids bind via peptide bonds
More informationBundesdruckerei Berlin
Europaisches Patentamt European Patent Office Office europeen des brevets Publication number: 0 289 353 A*2 EUROPEAN PATENT APPLICATION (5) Application number: 88303945.5 @ Date of filing: 29.04.88 @ Int.CI.*:
More informationSyllabus. 1. Occurrence and Functions of Peptides in Nature and Every Day Life hormones, neurotransmitters, therapeutics, artificial sweetener,
Syllabus 1. ccurrence and Functions of Peptides in ature and Every Day Life hormones, neurotransmitters, therapeutics, artificial sweetener, 2. Peptide Synthesis a) Aspartam: Properties of amino acids;
More informationSimple, economical and flexible apparatus for solid phase peptide synthesis
Indian Journal of Chemistry Vol. 46B, July 2007, pp. 1143-1147 Simple, economical and flexible apparatus for solid phase peptide synthesis Kota Satyanarayana*, K V R C Rajesh Kumar & Ch Venkanna Natco
More informationDifficulties In Synthesis and Characterization
HACETTEPE JOURNAL OF BIOLOGY AND CHEMISTRY Hacettepe J. Biol. & Chem., 2008, 36 (4), 329-337 Research Article Difficulties In Synthesis and Characterization of Viral Capsid Peptides Zafer Ömer Özdemir*,
More informationTetrabutylammoniumbromide mediated Knoevenagel condensation in water: synthesis of cinnamic acids
Tetrabutylammoniumbromide mediated Knoevenagel condensation in water: synthesis of cinnamic acids Monika Gupta a * and Basant Purnima Wakhloo b a Department of Chemistry, University of Jammu, Jammu-180
More informationMicrowave Assisted Peptide Synthesis. Sanjukta Ghosh Green Chemistry 671 December 8, 2011
Microwave Assisted Peptide Synthesis Sanjukta Ghosh Green Chemistry 671 December 8, 2011 Overview I. What are peptides and why are they important II. III. IV. Conventional method of peptide synthesis :
More informationThe D-glucosamine-derived pyridyl-triazole@palladium recoverable catalyst for Mizoroki-Heck reactions under solvent-free conditions
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 204 Supporting Information The D-glucosamine-derived pyridyl-triazole@palladium recoverable catalyst
More informationHow To Use An Acquity Qda Detector
Mass-Directed Isolation of a Synthetic Peptide Using the ACQUITY QDa Detector Jo-Ann M. Jablonski and Andrew J. Aubin Waters Corporation, Milford, MA, USA APPLICATION BENEFITS The ACQUITY QDa Detector
More informationCombinatorial Chemistry and solid phase synthesis seminar and laboratory course
Combinatorial Chemistry and solid phase synthesis seminar and laboratory course Topic 1: Principles of combinatorial chemistry 1. Introduction: Why Combinatorial Chemistry? Until recently, a common drug
More informationFast conventional Fmoc solid-phase peptide synthesis with HCTU
Journal of Peptide Science J. Pept. Sci. 2008; 14: 97 101 Published online 24 September 2007 in Wiley InterScience (www.interscience.wiley.com)..921 Fast conventional Fmoc solid-phase peptide synthesis
More informationSpecific Peptide-Bond Cleavage by Microwave Irradiation in Weak Acid Solution
Journal of Protein Chemistry, VoL 11, No. 1, 1992 Specific Peptide-Bond Cleavage by Microwave Irradiation in Weak Acid Solution Chi-Yue Wu, 1 Shui-Tein Chen, r Shyh-Horng Chiou, 1'2 and Kung-Tsung Wang
More informationSupporting information. Cyclic peptide-polymer conjugates: grafting to VS grafting from
Supporting information Cyclic peptide-polymer conjugates: grafting to VS grafting from Sophie C. Larnaudie, a Johannes C. Brendel, a,c Katrina A. Jolliffe* b and Sébastien Perrier* a,c a Department of
More informationCEM, First in Microwave Peptide Synthesis
CEM, First in Microwave Peptide Synthesis In 2002, a CEM biochemist named Jonathan Collins presented his concept of a microwave-assisted peptide synthesis system to several colleagues. Collins concept
More informationLabelling of peptides with CyDye fluors for fluorescent applications on the LEADseeker Homogeneous Imaging System
Issue No. 7 abelling of peptides with CyDye fluors for fluorescent applications on the EADseeker Homogeneous Imaging System EADseeker TM homogeneous imaging system is a digital imager comprising a chargecoupled
More informationT3P Propane Phosphonic Acid Anhydride
Technology StrengthS T3P Propane Phosphonic Acid Anhydride The coupling agent of the future Coupling and water removal are synthesis tools that stand at the cutting edge of purity and cost effective manufacture
More information4026 Synthesis of 2-chloro-2-methylpropane (tert-butyl chloride) from tert-butanol
4026 Synthesis of 2-chloro-2-methylpropane (tert-butyl chloride) from tert-butanol OH + HCl Cl + H 2 O C 4 H 10 O C 4 H 9 Cl (74.1) (36.5) (92.6) Classification Reaction types and substance classes nucleophilic
More informationA Ratiometric NMR ph Sensing Strategy Based on Slow- Proton-Exchange (SPE) Mechanism
Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2015 A Ratiometric NMR ph Sensing Strategy Based on Slow- Proton-Exchange (SPE) Mechanism Loïse
More informationSupplemental Material: peptide synthesis
Supplemental Material: peptide synthesis Synthesis of MMAE containing ACPPs (Scheme 1) The peptides were synthesized by using regular solid phase Fmoc peptide synthesis. Peptides that were used for fluorescence
More informationSupplementary Information for
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Supplementary Information for Doubly Responsive Polymersomes towards Monosaccharides and
More informationMelting points (m.p.) were determined using a Reichert hot-stage melting point
Supporting information 1.0 General experimental 1.1 Instrumentation Melting points (m.p.) were determined using a Reichert hot-stage melting point apparatus and are uncorrected. Infrared spectra (IR) spectra
More informationTENDER DOCUMENT PURCHASING EQUIPMENT FOR PEPTIDE SYNTHESIS
TENDER DOCUMENT PURCHASING EQUIPMENT FOR PEPTIDE SYNTHESIS for Barents BioCentre Section 1 Description of the purchase 1.1. Introduction The Northern Research Institute (NORUT) P.O. Box 6434 Forskningsparken,
More informationHigh-Yield Synthesis and Purification of an -Helical Transmembrane Domain
Analytical Biochemistry 293, 102 108 (2001) doi:10.1006/abio.2001.5122, available online at http://www.idealibrary.com on High-Yield Synthesis and Purification of an -Helical Transmembrane Domain Lillian
More informationRapid Flow-Based Peptide Synthesis
Rapid Flow-Based Peptide Synthesis The MIT Faculty has made this article openly available. Please share how this access benefits you. Your story matters. Citation Simon, Mark D., Patrick L. Heider, Andrea
More informationDr. Rita P.-Y. Chen Institute of Biological Chemistry Academia Sinica
PEPTIDE SYNTHESIS Dr. Rita P.-Y. Chen Institute of Biological Chemistry Academia Sinica 1 Solution phase chemistry -Time consuming: isolation and purification at each step -Low yield: can t drive reaction
More informationMaterials and Methods. Protocol for Fmoc- based solid- phase peptide synthesis
Materials and Methods All commercially available materials (Aldrich, TCI, ovabiochem, Fluka ) were used without further purification. All solvents were reagent grade or PLC grade (Fisher ). Anhydrous TF,
More informationDepartment of Chemistry and Pharmacy - Universität Regensburg. Karoly Agoston, Armin Geyer, Burkhard König, Michael Kruppa and Andreas Grauer
Department of Chemistry and Pharmacy - Universität Regensburg CMBIATRIAL CHEMISTRY AD SLID PHASE SYTHESIS: SEMIAR AD LABRATRY CURSE Karoly Agoston, Armin Geyer, Burkhard König, Michael Kruppa and Andreas
More informationWorking with Hazardous Chemicals
A Publication of Reliable Methods for the Preparation of Organic Compounds Working with Hazardous Chemicals The procedures in Organic Syntheses are intended for use only by persons with proper training
More informationSynthesis of Leucine Zippers and Leucine Zipper Dendrimers
Supplementary Materials Helical Supramolecules and Fibers Utilizing Leucine-Zipper Displaying Dendrimers Min Zhou, David Bentley, Indraneel Ghosh Contribution from the Department of Chemistry, University
More informationSynthesis and Antimicrobial Activity of 7-Amino cephalosporanic Acid Derivatives of Amino Acids and Peptides
Asian Journal of Chemistry Vol. 22, No. 4 (2010), 2914-2918 Synthesis and Antimicrobial Activity of 7-Amino cephalosporanic Acid Derivatives of Amino Acids and Peptides M. HIMAJA*, SIDDHARTH DESAI, A.
More informationCyclic peptides containing a d-sugar amino acid synthesis and evaluation as artificial receptors
Tetrahedron 61 (2005) 863 874 Cyclic peptides containing a d-sugar amino acid synthesis and evaluation as artificial receptors Johan F. Billing and Ulf J. Nilsson* Organic and Bioorganic Chemistry, Lund
More informationGuidance for Industry
Guidance for Industry for the Submission of Chemistry, Manufacturing, and Controls Information for Synthetic Peptide Substances Center for Drug Evaluation and Research (CDER) Center for Biologics Evaluation
More informationand its application in the synthesis of Nilotinib intermediate
Electronic upplementary Material (EI) for RC Advances. This journal is The Royal ociety of Chemistry 204 upporting Information An efficient D-glucosamine-based copper catalyst for C-X couplings and its
More information2. Couple the two protected amino acids.
General Considerations The Strategy of Peptide Synthesis Making peptide bonds between amino acids is not difficult. The challenge is connecting amino acids in the correct sequence. andom peptide bond formation
More informationAlkoxycarbonylation of Ethylene with Cellulose in Ionic Liquids
Supplementary data Alkoxycarbonylation of Ethylene with Cellulose in Ionic Liquids Anna sichow and Stefan Mecking* Chair of Chemical Materials Science, Dept. of Chemistry, University of Konstanz, 78464
More informationl 4-minute cycle time l 90% solvent reduction Remarkably fast Automated Microwave Peptide Synthesizer
Automated Microwave Peptide Synthesizer CEM is transforming the way chemists perform peptide synthesis once again with the introduction of the Liberty Blue Microwave Peptide Synthesizer. More than just
More informationSupporting Information. Minimum active structure of insulin-like. peptide 5 (INSL5)
Supporting Information Minimum active structure of insulin-like peptide 5 (INSL5) Alessia Belgi 1,2, Ross A.D. Bathgate *1,2,3, Martina Kocan *4, Nitin Patil 1,5, Suode Zhang 1, Geoffrey W. Tregear 1,2,
More informationPeptide synthesis, radiolabelling and radiochemical analysis
SUPPLEMENTAL DATA MATERIALS AND METHODS Peptide synthesis, radiolabelling and radiochemical analysis Solid phase synthesis of peptides was carried out on using ABI 433A peptide synthesizer, on a preloaded
More informationPrepatellamide A, a new cyclic peptide from the ascidian Lissoclinum patella
Vol. 43 No. 6 SCIENCE IN CHINA (Series B) December 2000 Prepatellamide A, a new cyclic peptide from the ascidian Lissoclinum patella FU Xiong ( ), SU Jingyu ( ) & ZENG Longmei ( ) Department of Chemistry,
More informationEXPERIMENT 5: DIPEPTIDE RESEARCH PROJECT
EXPERIMENT 5: DIPEPTIDE RESEARCH PROJECT Pre-Lab Questions: None. 64 I. Background Information DIPEPTIDE RESEARCH PROJECT Methods developed by organic chemists for the synthesis of biopolymers have had
More informationSupplemental Material for Jiang et al, Tumor Imaging via Proteolytic Activation of Cell Penetrating Peptides
Supplemental Material for Jiang et al, Tumor Imaging via Proteolytic Activation of Cell Penetrating Peptides Reagents Fmoc protected amino acids and synthesis resins were purchased from EMD Chemicals Inc.
More informationOxyma: An Efficient Additive for Peptide Synthesis to Replace the Benzotriazole-Based HOBt and HOAt with a Lower Risk of Explosion [1]
DOI: 10.1002/chem.200900614 Oxyma: An Efficient Additive for Peptide Synthesis to Replace the Benzotriazole-Based HOBt and HOAt with a Lower Risk of Explosion [1] Ramon Subirós-Funosas, [a, b] Rafel Prohens,
More informationEfficient Synthesis of Peptides with 4-Methylpiperidine as Fmoc Removal Reagent by Solid Phase Synthesis
J. Mex. Chem. Soc. 2014, 58(4), 386-392 386 Article J. Mex. Chem. Soc. 2014, 58(4) Cristian 2014, Francisco Sociedad Vergel Química Galeano de México et al. ISSN 1870-249X Efficient Synthesis of Peptides
More informationDipeptide Synthesis. polarized light (Figure 2).
Dipeptide Synthesis + Scheme 1: Peptide synthesis without carboxyl activation + 2 Throughout your organic chemistry tenure you have been taught the underlying principles necessary to construct simple organic
More informationProtection of the Amide Side-Chain of Asparagine with the 1-Tetralinyl Group in the Solid-Phase Peptide Synthesis of Lysine-Vasopressin
A.O. Yusuf, B.M. Bhatt and P.M. Gitu, S. Afr. J. Chem., 2002, 55, 87-96, RESEARCH ARTICLE Protection
More informationThe Peptides Vol. 2: Analysis, Synthesis, Biology: Special Methods in Peptide Synthesis
The Peptides Vol. 2: Analysis, Synthesis, Biology: Special Methods in Peptide Synthesis Download: The Peptides Vol. 2: Analysis, Synthesis, Biology: Special Methods in Peptide Synthesis PDF ebook The Peptides
More informationPeptide purification strategies
Särö Conference 2009 Peptide purification strategies Ulf Altenhöner Lonza Exclusive Synthesis R&D Outline Introduction Integrated process development Model-based process development Inspiration Conclusions
More informationDEVELOPMENT OF MICROWAVE-ASSISTED SYNTHESIS METHODS FOR PREPARATION OF PEPTIDES. Ph.D. thesis BERNADETT BACSA
DEVELOPMENT OF MICROWAVE-ASSISTED SYNTHESIS METHODS FOR PREPARATION OF PEPTIDES Ph.D. thesis BERNADETT BACSA Supervisors: Dr. Gábor Dibó associate professor ELTE Department of Organic Chemistry Dr. Gábor
More informationAspects of industrial purification of peptides using large-scale chromatography. Lars Andersson and Jonas Persson
Aspects of industrial purification of peptides using large-scale chromatography Introduction By Lars Andersson and Jonas Persson PolyPeptide Laboratories (Sweden) AB PO Box 30089 SE-200 61 LIMHAMN SWEDEN
More informationGuide to Reverse Phase SpinColumns Chromatography for Sample Prep
Guide to Reverse Phase SpinColumns Chromatography for Sample Prep www.harvardapparatus.com Contents Introduction...2-3 Modes of Separation...4-6 Spin Column Efficiency...7-8 Fast Protein Analysis...9 Specifications...10
More information(51) Int Cl.: C08F 8/00 (2006.01) C07K 17/08 (2006.01) C07K 1/04 (2006.01)
(19) Europäisches Patentamt European Patent Office Office européen des brevets (11) EP 1 263 800 B1 (12) EUROPEAN PATENT SPECIFICATION (4) Date of publication and mention of the grant of the patent: 08.11.06
More informationexperiment5 Understanding and applying the concept of limiting reagents. Learning how to perform a vacuum filtration.
81 experiment5 LECTURE AND LAB SKILLS EMPHASIZED Synthesizing an organic substance. Understanding and applying the concept of limiting reagents. Determining percent yield. Learning how to perform a vacuum
More informationadvanced separation chemistry for life sciences
Fluorous Based Peptide Synthesis and Immobilization in the Formation of a Protease Microarray Marvin S. Yu August 2009 advanced separation chemistry for life sciences Acknowledgements Fluorous Technologies,
More informationSynthesis and application of photoproline - a photoactivatable derivative of proline
Issue in onor of Prof. einz eimgartner ARKIVC 2011 (vi) 130-136 Synthesis and application of photoproline - a photoactivatable derivative of proline Benjamin Van der Meijden and John A. Robinson* Chemistry
More information1,2-Dimethylindole-3-sulfonyl (MIS) as protecting group for the side chain of arginine
1,2-Dimethylindole-3-sulfonyl (MIS) as protecting group for the side chain of a... (D... Page 1 of 10 Organic & Biomolecular Chemistry Journals Organic & Biomolecular Chemistry Advance Articles DOI: 10.1039/b904836g
More informationExpedient Solid-Phase Synthesis of Fluorogenic Protease Substrates Using the 7-Amino-4-carbamoylmethylcoumarin (ACC) Fluorophore
910 J. Org. Chem. 2002, 67, 910-915 Expedient Solid-Phase Synthesis of Fluorogenic Protease Substrates Using the 7-Amino-4-carbamoylmethylcoumarin (ACC) Fluorophore Dustin J. Maly, Francesco Leonetti,
More informationPS3 Peptide Synthesizer QUICK START GUIDE
PS3 TM Peptide Synthesizer QUICK START GUIDE TM PS3 Peptide Synthesizer QUICK START GUIDE 2006 Protein Technologies, Inc. 4675 S. Coach Dr. Tucson, AZ 85714 USA All Rights Reserved. DOC #9030005 Rev 01
More informationPeptide Nucleic Acid Microarrays
PNA Microarrays 283 21 Peptide Nucleic Acid Microarrays Anette Jacob, Ole Brandt, Achim Stephan, and Jörg D. Hoheisel Summary A fast and economical procedure for the production of peptide nucleic acid
More informationSynthesis of Combinatorial Libraries of Vinylogous Sulfonamidopeptides (vs-peptides)
Synthesis of Combinatorial Libraries of Vinylogous Sulfonamidopeptides (vs-peptides) Cesare Gennari* a, b, c, Chiara Longari a, Stefano Ressel a, Barbara Salom a, Umberto Piarulli a, c, Simona Ceccarelli
More informationNaturally occuring depsipeptides exhibit interesting
Simple Machine-Assisted Protocol for Solid-Phase Simple Synthesis Machine-Assisted of Depsipeptides Protocol for Solid-Phase Synthesis of Depsipeptides Jan Spengler, 1 Beate Koksch, 2 Fernando Albericio
More informationDetermining the Structure of an Organic Compound
Determining the Structure of an Organic Compound The analysis of the outcome of a reaction requires that we know the full structure of the products as well as the reactants In the 19 th and early 20 th
More informationELECTRONIC SUPPLEMENTARY INFORMATION
ELECTRONIC SUPPLEMENTARY INFORMATION General.. 1 1 HNMR titration fitplots.. 2 1 HNMR titration Job plots... 2 1 HNMR spectra of 1 + TBAacetate. 3 Isothermal Titration Calorimetry.. 3 High Resolution Mass
More informationApplication of a New Immobilization H/D Exchange Protocol: A Calmodulin Study
Application of a New Immobilization H/D Exchange Protocol: A Calmodulin Study Jiang Zhao; Mei Zhu; Daryl E. Gilblin; Michael L. Gross Washington University Center for Biomrdical and Bioorganic Mass Spectrometry:
More informationSupporting Information
Supporting Information Chemoproteomics-Enabled Discovery of a Potent and Selective Inhibitor of the DNA Repair Protein MGMT Chao Wang +, Daniel Abegg +, Dominic G. Hoch, and Alexander Adibekian* ange_201511301_sm_miscellaneous_information.pdf
More informationSynthesis of Cyclic Antifreeze Glycopeptide and Glycopeptoids and Their Ice Recrystallization Inhibition Activity
SAR of Cyclic Glycopeptide Bull. Korean Chem. Soc. 2012, Vol. 33, No. 11 3565 http://dx.doi.org/10.5012/bkcs.2012.33.11.3565 Synthesis of Cyclic Antifreeze Glycopeptide and Glycopeptoids and Their Ice
More informationCOMBINING CYCLIC PEPTIDES WITH METAL COORDINATION
COMBINING CYCLIC PEPTIDES WITH METAL COORDINATION A Thesis Presented to The Academic Faculty by Kimberly Ann Arrowood In Partial Fulfillment of the Requirements for the Master s Degree in Chemistry in
More informationA Complete Solution for Method Linearity in HPLC and UHPLC
Now sold under the Thermo Scientific brand A Complete Solution for Method Linearity in HPLC and UHPLC Frank Steiner, Fraser McLeod, Tobias Fehrenbach, and Andreas Brunner Dionex Corporation, Germering,
More informationPrecipitation Titration: Determination of Chloride by the Mohr Method by Dr. Deniz Korkmaz
Precipitation Titration: Determination of Chloride by the Mohr Method by Dr. Deniz Korkmaz Introduction Titration is a process by which the concentration of an unknown substance in solution is determined
More information