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) Glucagon: Solid phase peptide synthesis c) Fuzeon, an anti IV 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.. Wennemers 6
2 Die Entdeckung von Aspartam - Serendipity in Science Gastrin = -Glp-Gly-Pro-Trp-Leu-Glu-Glu-Glu-Glu-Glu-Ala-Tyr-Gly-Trp-Met-Asp-Phe- 2 ormon, das im Magen durch G-Zellen freigesetzt wird und die Bildung von Magensäure anregt. für physiologische Aktivität nur die vier C-terminalen Aminosäuren notwendig -Trp-Met-Asp-Phe James M. Schlatter (G. D. Searle & Company, heute: Monsanto) sucht nach einem Wirkstoff gegen Magengeschwüre und stellt -Asp-Phe-C 3 her...und tut etwas, was man nicht tun sollte... 7 Prof.. Wennemers
3 Solution Phase: Calcitonin (salmon) CSLSTCVLGKLSQELKLQTYPTTGSGTP slide by Dr. Thomas Früh, CE Bachem BACEM olding AG Company Presentation Seite 8 September 2012
4 Calcitonin Adversary of calcitonin: Parathyroid ormon (PT) From:. Sewald,.-D. Jakubke, Peptides: Chemistry and Biology, 2 nd Ed., Wiley-VC, Weinheim,
5 Solution Phase: Calcitonin (salmon) Z Me Z Z Me Z Me Z Z Me Z Boc Me Z Me Z Boc Z Boc Z- - 2 Boc Calcitonin (protected) Calcitonin (crude) Calcitonin (purified) slide by Dr. Thomas Früh, CE Bachem BACEM olding AG Company Presentation Seite 10 September 2012
6 Solution Phase Peptide Synthesis Scale - Produced since Synthetic steps 104 Calcitonin - Purification CCD two-dim. PLC - Derivatives needed 158 kg for the production of 1kg - Time for completion 2.5 years slide by Dr. Thomas Früh, CE Bachem BACEM olding AG Company Presentation Seite 11 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) Glucagon: Solid phase peptide synthesis c) Fuzeon, an anti IV 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.. Wennemers 12
8 Peptidsynthesizer 1966 Solid Phase Peptide Synthesis (SPPS) (obelprize for Chemistry 1984: Bruce Merrifield) Prof.. Wennemers 13
9 Solid Phase Peptide Synthesis (SPPS) Fmoc/tBu Strategie in the example: Wang Linker Cl Wang Linker 1 Fmoc C 2 DMF Cs Fmoc 1 Linker Piperidine:DMF 1:4 (1x 3 min, 1x 7 min) 2 1 Linker 3 equiv. 2 Fmoc C 2 3 eq. PyBP, 3 eq. ipr 2 Et Fmoc 2 1 Linker repeat Fmoc deprotection/aa couplings to desired peptide length 2 n 2 1 Linker 95% TFA 3 (scavengers) 2 side-chain deprotected peptide n 1 Prof.. Wennemers 14
10 Kupplungsreagenzien Carbodiimide C = = cyclohexyl:, -Di-Cyclohexyl Carbodiimid (DCC) = = iso-propyl:, -Di-Isopropyl Carbodiimid (DIC) = Et, = C 2 C 2 C 2 Me 2 : -Ethyl- -(3-Dimethylaminopropyl) Carbodiimid (EDC) Phosphonium eagenzien Guanidinium/Uronium eagenzien PF 6 P Me 2 Me 2 Me 2 PF 6 P PF 6 PF 6 BP (Castro`s eagent) Prof.. Wennemers PyBP P Et Et DEPBT BTU ATU BF 4 TBTU 15
11 Commonly used acid sensitive protecting groups for the functional groups of the amino acid side chains Fmoc: α- group Boc: Lysine, Tryptophan, istidine Pbf: Arginine Trt: Cysteine, Aspartic acid, Glutamic acid Acm: Cysteine tbu: Serine, Threonine, ydroxyproline, Tyrosine Prof.. Wennemers 16
12 Linker für die Festphasensynthese Me Cl Ph Wang SASI Chlorotrityl Me Me ink Amide ycram 2 Prof.. Wennemers 17 o-itrobenzyl Kenner Safety Catch S
13 Peptidsynthese an fester Phase (obelpreis für Chemie 1984 für Bruce Merrifield) Peptidsynthesizer 1966 Prof.. Wennemers heute 18
14 Examples of Crude Purity slide by Dr. Thomas Früh, CE Bachem BACEM olding AG Company Presentation Seite 19 September 2012
15 Solid Phase: Glucagon (1-29, human) SQGTFTSDYSKYLDSAQDFVQWLMT slide by Dr. Thomas Früh, CE Bachem BACEM olding AG Company Presentation Seite 20 September 2012
16 Insulin and Glucagon Glucagon (Secre3n Family) Insulin (Insulin Superfamily) inac+ve hexameric form bound to Zn 2+ : BACEM olding AG Company Presentation Seite 21 September
17 Comparison: Solution vs. Solid Phase Calcitonin Glucagon - Produced since Synthetic steps Purification CCD two-dim. PLC three-dim. PLC - Derivatives needed 158 kg 29 kg for the production of 1kg - Time for completion 2.5 years 0.6 years BACEM olding AG Company Presentation Seite 22 September 2012
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