Enantiomerically enriched α-vinyl amino acids via lipase-mediated "reverse transesterification"

David B Berkowitz, James A. Pumphrey, Quanrong Shen

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

Reduction of protected α-vinyl amino acids produces "neopentyl" alcohols that may be enriched in the L-antipode by lipase-mediated acylation with vinyl acetate. Subsequent deacetylation, oxidation and hydrolysis yields enantiomerically enriched L-α-vinyl amino acids.

Original languageEnglish (US)
Pages (from-to)8743-8746
Number of pages4
JournalTetrahedron Letters
Volume35
Issue number47
DOIs
StatePublished - Nov 21 1994

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Transesterification
Lipase
Amino Acids
Acylation
Hydrolysis
Oxidation
vinyl acetate
2,2-dimethylpropanol

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Enantiomerically enriched α-vinyl amino acids via lipase-mediated "reverse transesterification". / Berkowitz, David B; Pumphrey, James A.; Shen, Quanrong.

In: Tetrahedron Letters, Vol. 35, No. 47, 21.11.1994, p. 8743-8746.

Research output: Contribution to journalArticle

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