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Synlett 2007(16): 2517-2520
DOI: 10.1055/s-2007-986631
DOI: 10.1055/s-2007-986631
LETTER
© Georg Thieme Verlag Stuttgart · New York
Avoidance of Epimerization in the Synthesis of Peptide Thioesters Using Fmoc Protection
Further Information
Received
5 July 2007
Publication Date:
28 August 2007 (online)
Publication History
Publication Date:
28 August 2007 (online)
Abstract
An efficient procedure for the conversion of protected peptides into thioesters has been developed which dramatically reduces the occurrence of C-terminal epimerization.
Key words
peptide - thioester - stereoselective synthesis - solvent effects - proteins
- 1
Dawson PE.Kent SBH. Annu. Rev. Biochem. 2000, 69: 923 - 2
Dawson PE.Muir TW.Clarklewis I.Kent SBH. Science 1994, 266: 776 - 3
Eggelkraut-Gottanka R.Klose A.Beck-Sickinger AG.Beyermann M. Tetrahedron Lett. 2003, 44: 3551 - 4
Mezo AR.Cheng RP.Imperiali B. J. Am. Chem. Soc. 2001, 123: 3885 ; note that epimerization of some sequences was observed using this procedure - 5
Kleanthous C.Walker D. Trends Biochem. Sci. 2001, 26: 624 -
6a
Alsina J.Albericio F. Biopolymers 2003, 71: 454 -
6b
Swinnen D.Hilvert D. Org. Lett. 2000, 2: 2439 -
7a
Ingenito R.Bianchi E.Fattori D.Pessi A. J. Am. Chem. Soc. 1999, 121: 11369 -
7b
Shin Y.Winans KA.Backes BJ.Kent SBH.Ellman JA.Bertozzi CR. J. Am. Chem. Soc. 1999, 121: 11684 - 8
Quaderer R.Hilvert D. Org. Lett. 2001, 3: 3181 - 9
Mezzato S.Schaffrath M.Unverzagt C. Angew. Chem. Int. Ed. 2005, 44: 1650 - 10
Jones JH.Woitty MJ. J. Chem. Soc., Perkin Trans. 1 1979, 3203 - 11 A related SPh equivalent of 5 has been synthesized and used in the formation of thioesters although significant side reactions occurred in the reported case. See:
Biancalana S.Hudson D.Songster MF.Thompson SA. Lett. Pept. Sci. 2001, 7: 291 - 12
Daffe V.Fastrez J. J. Chem. Soc., Perkin Trans. 2 1983, 783 - 13
Li HT.Jiang XH.Ye YH.Fan CX.Romoff T.Goodman M. Org. Lett. 1999, 1: 91