A simple and efficient synthesis of an Asp-Gly dipeptide mimetic

John M. Ndungu, Xuyuan Gu, Dustin E. Gross, Jinfa Ying, Victor J. Hruby

Research output: Contribution to journalArticle

10 Scopus citations

Abstract

Alkylation of Nα-Boc protected aspartic acid with allyl bromide in the presence of lithium bis(trimethylsilyl)amide (LHMDS) and hexamethylphosphoramide (HMPA) afforded chiral β-allyl substituted aspartic acid in good yields. After deprotection of the Nα-Boc group and reprotection as a trifluoroacetamide, the terminal alkene was oxidized to an aldehyde. The aldehyde was then coupled with L-cysteine through a cascade three-bond formation process to afford aspartic acid-glycine bicyclic dipeptide mimetics.

Original languageEnglish (US)
Pages (from-to)3245-3247
Number of pages3
JournalTetrahedron Letters
Volume45
Issue number16
DOIs
StatePublished - Apr 12 2004

Keywords

  • Bicyclic dipeptide
  • Cholecystokinin
  • Trifluoroacetamide
  • β-substituted aspartic acid

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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