Methods for enhancing ring closing metathesis yield in peptides: Synthesis of a dicarba human growth hormone fragment

International Journal of Peptide Research and Therapeutics

Volumn 16, Issue 3, 2010, Pages 133-144

  Van Lierop, Bianca J ^a   Whelan, Amanda N ^a,b   Andrikopoulos, Sofianos ^c   Mulder, Roger J ^b   Jackson, W Roy ^a   Robinson, Andrea J ^a  

^a MONASH UNIVERSITY   (Australia)

^b CSIRO   (Australia)

^c UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

Anti obesity; AOD9604; Cyclic peptides; Dicarba peptides; Microwave irradiation; Pseudoproline ( Pro) residues; Ring closing metathesis (RCM)

Indexed keywords

ADENOHYPOPHYSIS HORMONE; DICARBA HUMAN GROWTH HORMONE[176-191][176 TYROSINE]; HUMAN GROWTH HORMONE[176-191][176 TYROSINE]; PLACEBO; PROLINE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; CONFERENCE PAPER; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; DOSE RESPONSE; DRUG MECHANISM; DRUG SAFETY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; HYDROGEN BOND; MALE; MASS SPECTROMETRY; MICROWAVE IRRADIATION; MOUSE; NONHUMAN; OBESITY; PROTEIN METABOLISM; PROTON NUCLEAR MAGNETIC RESONANCE; RESIDUE ANALYSIS; RING CLOSING METATHESIS; STRUCTURE ANALYSIS;

EID: 79951553842     PISSN: 15733149     EISSN: 15733904     Source Type: Journal    
DOI: 10.1007/s10989-010-9215-y     Document Type: Conference Paper

References (25)

1. Armishaw CJ, Daly NL, Nevin ST, Adams DJ, Craik DJ, Alewood PF (2006) α-Selenoconotoxins, a new class of potent α7 neuronal nicotinic receptor agonists. J Biol Chem 281:14136-14143 (Pubitemid 43848341)
2. Barth T, Servitova L (1975) Metabolic stability of some oxytocin analogues in homogenates of rat and kidney liver. Collect Czech Chem Commun 40:215-217
3. Brik A (2008) Metathesis in peptides and petiodomimetics. Adv Synth Catal 350:1661-1675
4. Craik DJ (2006) Seemless proteins tie up their loose ends. Science 311:1563-1564
5. Dumy P, Keller M, Ryan DE, Rohwedder B, Wöhr T, Mutter M (1997) Pseudo-prolines as a molecular hinge: reversible induction of cis amide bonds into peptide backbones. J Am Chem Soc 119:918-925 (Pubitemid 27107214)
6. Hossain MA, Rosengren KJ, Zhang S, Bathgate RAD, Tregear GW, van Lierop BJ, Robinson AJ, Wade JD (2009) Solid phase synthesis and structural analysis of novel A-chain dicarba analogs of human relaxin-3 (INSL7) that exhibit full biological activity. Org Biomol Chem 7:1547-1553
7. Humphrey JM, Chamberlin AR (1997) Chemical synthesis of natural product peptides: coupling methods for the incorporation of noncoded amino acids into peptides. Chem Rev 97:2243-226006 (Pubitemid 127661210)
8. Illesinghe J, Guo CX, Garland R, Ahmed A, van Lierop BJ, Elaridi J, Jackson WR, Robinson AJ (2009) Metathesis assisted synthesis of cyclic peptides. Chem Commun 295-297
9. Korner J, Aronne RJ (2004) Pharmacological approaches to weight reduction: therapeutic targets. J Clin Endocrinol Metab 89:2616-2621 (Pubitemid 38766340)
10. Li P, Roller PP (2002) Cyclization strategies in peptide derived drug design. Curr Top Med Chem 2:325-341
11. Li P, Roller PP, Xu J (2002) Current synthetic approaches to peptide and peptiomimetics cyclisation. Curr Org Chem 6:411-440 (Pubitemid 34495484)
12. MacRaild CA, Illesinghe J, van Lierop BJ, Townsend AL, Chebib M, Livett BG, Robinson AJ, Norton RS (2009) Structure and activity of (2,8)-dicarba-(3,12) -cystino α-ImI, an α-conotoxin containing a nonreducible cystine analogue. J Med Chem 53:755-762
13. Maruyama K, Nagasawa H, Suziki A (1999) 2,2'-Dipyridyl disulfide rapidly induces intramolecular disulfide bonds in peptides. Peptides 20:881-884 (Pubitemid 29378291)
14. Metabolic Pharmaceutical Ltd (2007) Options study for obesity drug: AOD9604. Metabolic Pharmaceutical Ltd., Melbourne
15. Miller SJ, Grubbs RH (1995) Synthesis of conformationally restricted amino acids and peptides employing olefin metathesis. J Am Chem Soc 117:5855-5856
16. Miller SJ, Blackwell HE, Grubbs RH (1996) Application of ringclosing metathesis to the synthesis of rigidified amino acids and peptides. J Am Chem Soc 118:9606-9614 (Pubitemid 26358319)
17. Moroder L, Besse D, Musiol HJ, Rudolph-Bohner S, Siedler F (1996) Oxidative folding of cystine-rich peptides vs regioselective cysteine pairing strategies. Biopolymers 40:207-234
18. Ogru E, Wilson JC, Heffernan M, Jiang W-J, Chalmers DK, Libinaki R, Ng F (2000) The conformational and biological analysis of a cyclic anti-obesity peptide from the C-terminal domain of the human growth hormone. J Pept Res 56:388-397
19. Robinson AJ, Elaridi J, van Lierop BJ, Mujcinovic S, Jackson WR (2007) Microwave-assisted RCM for the synthesis of carbocyclic peptides. J Pept Sci 13:280-285 (Pubitemid 46638199)
20. Robinson AJ, van Lierop BJ, Garland RD, Teoh E, Elaridi J, Illesinghe J, Jackson WR (2009) Regioselective formation of interlocked dicarba bridges in naturally occurring cyclic peptide toxins using olefin metathesis. Chem Commun 4293-4295
21. Sayyadi N, Skropeta D, Jolliffe KA (2005) N,O-isopropylidenated threonines as tools for peptide cyclisation: application to the synthesis of Mahafacyclin B. Org Lett 4:59-62
22. Schmiedeberg N, Kessler H (2002) Reversible backbone protection enables combinatorial solid-phase ring-closing metathesis reaction (RCM) in peptides. Org Lett 4:59-62
23. Skropeta D, Jolliffe KA, Turner P (2004) Pseudoprolines as removable turn inducers: tools for the cyclization of small peptides. J Org Chem 68:8804-8808
24. Wishart DS, Sykes BD, Richards FM (1992) The chemical shift index: a fast and simple method for the assignment of protein secondary structure through NMR spectroscopy. Biochemistry 31:1647-1651
25. Wöhr T, Wahl G, Nefzi A, Rohwedder B, Sato T, Sun X, Mutter M(1996) Pseudoprolines as solubilizing, structure-disrupting protection technique in peptide synthesis. J Am Chem Soc 118:9218-9227 (Pubitemid 26355114)