Syllabus. 1. Occurrence and Functions of Peptides in Nature and Every Day Life hormones, neurotransmitters, therapeutics, artificial sweetener,
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1 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; nomenclature; solution phase synthesis b) Cetrorelix, an anti cancer drug: Solid phase peptide synthesis c) Fuzeon, an anti HIV drug: Solution and solid phase peptide synthesis 3. Peptide Structures anostructured Materials Self-assembly a) Fuzeon: α-helices and coiled-coil structures b) Amyloids: β-sheets c) Collagen: PPII helices 4. Applications of Peptides in Chemistry, Biology and Material Sciences a) Peptide-based materials b) Therapeutically active peptides b) Cyclic peptides and cancer imaging c) Asymmetric Catalysis with Peptides Combinatorial chemistry Prof. H. Wennemers 7
2 Solution Phase: Calcitonin (salmon) Z H 3 H Me Z H H H 2 Z Me Z Me Z H Z- - 2 H 3 H Me Z- - 2 H 3 H H 2 Boc Me Z Me Z- -H Boc- - 2 H 3 H H Z- - 2 H H- -H 2 Boc H Z- -H 2 Boc H H- -H 2 Calcitonin (protected) Calcitonin (crude) Calcitonin (purified) slide by Dr. Thomas Früh, CE Bachem BACHEM Holding AG Company Presentation Seite 8 September 2012
3 Solution Phase: Calcitonin (salmon) CSLSTCVLGKLSQELHKLQTYPRTTGSGTP-H slide by Dr. Thomas Früh, CE Bachem BACHEM Holding AG Company Presentation Seite 9 September 2012
4 Calcitonin Adversary of calcitonin: Parathyroid Hormon (PTH) From:. Sewald, H.-D. Jakubke, Peptides: Chemistry and Biology, 2 nd Ed., Wiley-VCH, Weinheim,
5 Solution Phase Reactors slide by Dr. Thomas Früh, CE Bachem BACHEM Holding AG Page 11 February 2013
6 Solution Phase Peptide Synthesis Scale - Produced since Synthetic steps 104 Calcitonin - Purification CCD two-dim. HPLC - Derivatives needed 158 kg for the production of 1kg - Time for completion 2.5 years slide by Dr. Thomas Früh, CE Bachem BACHEM Holding AG Company Presentation Seite 12 September 2012
7 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; nomenclature; solution phase synthesis b) Cetrorelix, an anti cancer drug: Solid phase peptide synthesis c) Fuzeon, an anti HIV drug: Solution and solid phase peptide synthesis 3. Peptide Structures anostructured Materials Self-assembly a) Fuzeon: α-helices and coiled-coil structures b) Amyloids: β-sheets c) Collagen: PPII helices 4. Applications of Peptides in Chemistry, Biology and Material Sciences a) Peptide-based materials b) Therapeutically active peptides b) Cyclic peptides and cancer imaging c) Asymmetric Catalysis with Peptides Combinatorial chemistry Prof. H. Wennemers 13
8 Peptidsynthesizer 1966 Solid Phase Peptide Synthesis (SPPS) (obelprize for Chemistry 1984: Bruce Merrifield) Prof. H. Wennemers 14
9 Solid Phase Peptide Synthesis (SPPS) Fmoc/tBu Strategie in the example: Wang Linker Cl Wang Linker R 1 FmocH C 2 DMF Cs FmocH R 1 Linker Piperidine:DMF 1:4 (1x 3 min, 1x 7 min) H 2 R 1 Linker 3 equiv. R 2 FmocH C 2 H 3 eq. PyBP, 3 eq. ipr 2 Et FmocH R 2 H R 1 Linker repeat Fmoc deprotection/aa couplings to desired peptide length H 2 R n H R 2 H R 1 Linker H 95% TFA H H 3 (scavengers) H R 2 side-chain deprotected peptide R n R 1 Prof. H. Wennemers 15
10 Kupplungsreagenzien Carbodiimide R C R R = R = cyclohexyl:, -Di-Cyclohexyl Carbodiimid (DCC) R = R = iso-propyl:, -Di-Isopropyl Carbodiimid (DIC) R = Et, R = CH 2 CH 2 CH 2 Me 2 : -Ethyl- -(3-Dimethylaminopropyl) Carbodiimid (EDC) Phosphonium Reagenzien Guanidinium/Uronium Reagenzien PF 6 P Me 2 Me 2 Me 2 PF 6 P PF 6 PF 6 BP (Castro`s Reagent) Prof. H. Wennemers PyBP P Et Et DEPBT HBTU HATU BF 4 TBTU 16
11 Commonly used acid sensitive protecting groups for the functional groups of the amino acid side chains Fmoc: α-h group Boc: Lysine, Tryptophan, Histidine Pbf: Arginine Trt: Cysteine, Aspartic acid, Glutamic acid Acm: Cysteine tbu: Serine, Threonine, Hydroxyproline, Tyrosine Prof. H. Wennemers 17
12 Linker für die Festphasensynthese R R Me R Cl Ph Wang SASRI R Chlorotrityl Me Me H Rink Amide R H Hycram R 2 Prof. H. Wennemers 18 o-itrobenzyl Kenner Safety Catch H R H S H
13 Peptidsynthese an fester Phase (obelpreis für Chemie 1984 für Bruce Merrifield) Peptidsynthesizer 1966 Prof. H. Wennemers heute 19
14 Solid-Phase Peptide Synthesizer 150 L Reactor BACHEM Holding AG Company Presentation 1000 L Reactor Seite 20 September 2012 slide by Dr. Thomas Früh, CE Bachem
15 Typical Solid Phase Process Solid phase peptide synthesis Cleavage of crude peptide from the resin H 2 - P H 2 - -C 2 H Preparative HPLC purification Isolation, lyophilisation Z-Ala-Met-Pro-H #4: 61820/1/1a [modified by gen01] UV_VIS_1 mau WVL:220 nm %D: 0.0 % %C: 0.0 % Analytical testing release of product %B: 20.0 % Flow: ml/min min slide by Dr. Thomas Früh, CE Bachem BACHEM Holding AG Company Presentation Seite 21 September 2012
16 Cleavage and Separation slide by Dr. Thomas Früh, CE Bachem BACHEM Holding AG Company Presentation Seite 22 September 2012
17 Examples of Crude Purity slide by Dr. Thomas Früh, CE Bachem BACHEM Holding AG Company Presentation Seite 23 September 2012
18 Counter Current Distribution (CCD) slide by Dr. Thomas Früh, CE Bachem BACHEM Holding AG Company Presentation Seite 24 September 2012
19 Preparative HPLC 30 cm column BACHEM Holding AG Company Presentation 60 cm column Seite 25 September 2012 slide by Dr. Thomas Früh, CE Bachem
20 Product Isolation slide by Dr. Thomas Früh, CE Bachem BACHEM Holding AG Company Presentation Seite 26 September 2012
21 Solid Phase: Glucagon (1-29, human) HSQGTFTSDYSKYLDSRRAQDFVQWLMT slide by Dr. Thomas Früh, CE Bachem BACHEM Holding AG Company Presentation Seite 27 September 2012
22 Insulin and Glucagon Glucagon (Secre3n Family) Insulin (Insulin Superfamily) inac,ve hexameric form bound to Zn 2+ : BACHEM Holding AG Company Presentation Seite 28 September
23 Comparison: Solution vs. Solid Phase Calcitonin Glucagon - Produced since Synthetic steps Purification CCD two-dim. HPLC three-dim. HPLC - Derivatives needed 158 kg 29 kg for the production of 1kg - Time for completion 2.5 years 0.6 years BACHEM Holding AG Company Presentation Seite 29 September 2012
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