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Short asymmetric synthesis of a model monomeric unit for a/g peptide foldamers based on b -amino linked D-leucine – cis- g -butyrolactone g -acetic acid conjugate

Original Article

JOURNAL 809

Organic Communications
VOLUME & ISSUE
Year: 2017 Issue: 2 April-June
PAGES
p.99 - 103
DOI ADDRESS
http://doi.org/10.25135/acg.oc.13.16.12.474
STATISTICS
Viewed 1912 times.
AUTHORS
    Mohd Tajudin Mohd Ali, Siti Aisyah Aliasak and Allan Patrick G. Macabeo
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GRAPHICAL ABSTRACT

ABSTRACT

This synthetic work reports a concise, asymmetric synthesis of b -amino- g -butyrolactone acetic acid – D-leucine hybrid 1 which will serve as model starting template sub-unit for preparing a/g foldameric oligopeptides containing unnatural g -amino acid residues. The synthesis of cis-substituted 1 was successfully achieved in six linear steps with very good stereoinduction.

 KEYWORDS
  • cis- g -butyrolactone
  • foldamer
  • oligopeptide
  • asymmetric epoxide opening
  • g -amino acid