Desymmetrization of glycerol derivatives with peptide-based acylation catalysts

Org Lett. 2005 Jul 7;7(14):3021-3. doi: 10.1021/ol051061a.

Abstract

[reaction: see text] Nucleophile-loaded peptides have been evaluated as catalysts for the desymmetrization of glycerol derivatives through an enantioselective acylation process. Enantiomeric excesses of up to 97% have been obtained for the monoacylated products. A range of other substrates have been examined that shed light on the mechanistic basis of the desymmetrizations.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Acylation
  • Catalysis
  • Glycerol* / analogs & derivatives
  • Glycerol* / chemical synthesis
  • Glycerol* / chemistry
  • Indicators and Reagents
  • Lipase / metabolism
  • Molecular Structure
  • Peptides / chemistry*
  • Pseudomonas / enzymology
  • Stereoisomerism

Substances

  • Indicators and Reagents
  • Peptides
  • Lipase
  • Glycerol