Stereoselective synthesis of quaternary, α-vinyl amino acids and their α-(2'Z-fluoro)vinyl congeners: Promising candidates for PLP enzyme inactivation

David B. Berkowitz, Kannan R. Karukurichi, Roberto De La Salud-Bea, Gourhari Maiti, Jill M. McFadden, Michelle L. Morris

Research output: Chapter in Book/Report/Conference proceedingConference contribution

5 Scopus citations

Abstract

This chapter provides an overview of a program directed at the synthesis of amino acids (AA's) bearing a vinyl substituent in place of the usual α-proton. These quaternary amino acids are of interest, in and of themselves, as mechanism-based inhibitors of pyridoxal phosphate dependent enzymes, and also as building blocks for natural product or peptide synthesis. Importantly, these unnatural amino acids also serve as synthetic precursors for α-halovinyl AA's and α-oxiranyl AA's. Stereoselective synthetic methodology development in this area is highlighted and the initial performance of the α- (2'Z-fluoro)vinyl trigger in an amino acid decarboxylase (AADC) active site is described. Interestingly, at least for H. alvei lysine decarboxylase (LDC), inactivation with this trigger, along the α-branch, displays a marked enantio- dependence, with the L-antipode giving efficient inactivation, and its mirror image behaving as a simple substrate.

Original languageEnglish (US)
Title of host publicationAsymmetric Synthesis and Application of a-Amino Acids
PublisherAmerican Chemical Society
Pages288-303
Number of pages16
ISBN (Print)9780841269743
DOIs
StatePublished - Jun 14 2009

Publication series

NameACS Symposium Series
Volume1009
ISSN (Print)0097-6156
ISSN (Electronic)1947-5918

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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    Berkowitz, D. B., Karukurichi, K. R., De La Salud-Bea, R., Maiti, G., McFadden, J. M., & Morris, M. L. (2009). Stereoselective synthesis of quaternary, α-vinyl amino acids and their α-(2'Z-fluoro)vinyl congeners: Promising candidates for PLP enzyme inactivation. In Asymmetric Synthesis and Application of a-Amino Acids (pp. 288-303). (ACS Symposium Series; Vol. 1009). American Chemical Society. https://doi.org/10.1021/bk-2009-1009.ch018