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) spartam: 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) myloids: β-sheets c) ollagen: PPII helices 4. pplications of Peptides in hemistry, iology and Material Sciences a) Peptide-based materials b) Therapeutically active peptides (etrorelix, Fuzeon) c) yclic peptides and cancer targeting (imaging and therapy) d) symmetric atalysis with Peptides ombinatorial chemistry Prof.. Wennemers 90
2 xytocin Enkephalines S S 2 Dendrotoxin spartam Lisinopril 2 91 umerous functions but not a single naturally occuring catalytically active peptide known
3 ature s atalysts Peptides What can we learn from them? Efficient asymmetric catalysts?
4 Early Examples of Peptidic atalysts 3 Juliá, olonna, 1980 Roberts, 1995, erkessel, 2001 Epoxidation of chalcones n R Inoue, 1981 hydrocyanations ajos/parrish/wiechert/eder/sauer 1971 List, arbas, Lerner 2000,... 3 oc 3 3 y ldol and related reactions Miller, 1998 Ph 2 3 cylation and related reactions For reviews, see: Miller, hem. Rev. 2007, 107, Top. urr. hem. 2016, 372, 157. Wennemers, hem. ommun. 2011, 47, urr. pin. hem. iol. 2014, 22,
5 ucleophilic cylation atalysts Significantly higher activity compared to DMP 3 oc Ph 3 3 y 2 3 e.g. kinetic resolution of secondary or tertiary alcohols mechanistic proposal c 10 mol% cat., c 2 toluene c racemic + c c asymmetric phosphorylation reactions, azide conjugate additions, Stetter reactions, intermolecular aldehyde-imine cross-couplings, sulfinyl transfer reactions, Morita-aylis-illman reactions for a review see: S. J. Miller, cc. hem. Res. 2004, 37,
6 ucleophilic cylation atalysts - Remote Desymmetrization 5 mol% catalyst l 3, -30, 20h c 9.8 Å 80% yield, 95% ee catalyst oc Trt t u Ph Ph Ts.. Lewis,. hiu, M. Kubryk, J. alsells, D. Pollard,.K. Esser, J. Murry, R. Reamer, K.. ansen, S.J. Miller, J. m. hem. Soc. 2006, 128,
7 ucleophilic cylation atalysts - Site Selective Derivatization 11: 3rd Most Reactive - Erythromycin 2: Most Reactive - 2 4: 2nd Most Reactive - R R 5-10 mol% cat. R R R 2 catalyst oc 3 3 Ph oc R R 6 6 pyridine catalyst 1:2 1:2 >10:1 1:9 (58% yield of 2) 2:1 1:3.5 (28% yield of 2) 2 3 oc t u 5:1 1:>10 (53% yield of 2).. Lewis, S.J. Miller, ngew. hem. Int. Ed. 2006, 45, Prof.. Wennemers 96
8 ucleophilic cylation atalysts - Site Selective Derivatization.. Lewis, S.J. Miller IE 2006, 45, Prof.. Wennemers 97
9 Split-and-Mix Synthesis Á. Furka et al., Int. J. Pept. Res. 1991, 37, 487. Prof.. Wennemers 98
10 Encoded ombinatorial Synthesis M..J. hlmeyer, W.. Still, M.. Wigler, et al., Proc. atl. cad. Sci. US 1993, 90, P. estler, P.. artlett, W.. Still, J. rg. hem. 1994, 59, Prof.. Wennemers 99
11 Electrophoric Tag-Molecules and Linker TG ( 2 ) n l l 2 2 hν n = 7-10 l ( 2 ) n l l l TG n = 1-10 l l 3 TG ( 2 ) n n = 1-10 l l l 2 / 2 ( 2 ) n l n = 1 and 2 l F W.. Still, M.. Wigler et al. Proc. atl. cad. Sci. US 1993, 90, P. estler, P.. artlett, W.. Still J. rg. hem. 1994, 59,
12 Decoding of ombinatorial Libraries Encoding scheme 0001 la 0010 Val 0011 Leu 0100 Phe 0101 Pro 0110 Ser 1000 Thr 1001 Lys 1010 Gln 1100 sn tag alcohols ( 2 )n al x Ser - Pro - Pro - Leu W.. Still, M.. Wigler et al. Proc. atl. cad. Sci. US 1993, 90,
13 W. lark Still W. lark Still W.. Still, M.. Wigler et al. Proc. atl. cad. Sci. US 1993, 90, P. estler, P.. artlett, W.. Still J. rg. hem. 1994, 59, 4723.
14 Split-and-Mix Libraries - ow to find the catalyst? Prof.. Wennemers 103
15 IR-Thermography Insoluble colored reaction products hydrolysis air oxidation precipitates on bead J.P. Morken et al., Science erkessel et al., ngew. hem p-indicators Gels as reaction media slows down diffusion of colored reaction products S.J. Miller et al., JS 1999/2001.P. Davis et al., ngew. hem S. J. Miller et al., JS 2000
16 atalyst-substrate o-immobilisation reaction with nly compound 2 is an active catalyst! P. Krattiger,. Mcarthy,. Pfaltz,. Wennemers, ngew. hem. Int. Ed. 2003, 42,
Syllabus. 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;
Chemical BioIogy Peptides
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