Biosynthetic origins of C-P bond containing tripeptide K-26

Ioanna Ntai, M. Lisa Manier, David L. Hachey, Brian O. Bachmann*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

37 Scopus citations

Abstract

(Chemical Equation Presented) Primary metabolic precursors for K-26, a naturally occurring tripeptide phosphonic acid from Actinomyces sp. K-26, are investigated by heavy-atom isotope labeled substrate incorporation experiments. A highly sensitive selected reaction monitoring (SRM)-based method for isotopic incorporation estimation in natural products is reported. The incorporation of heavy-atom isotope labeled tyrosine compounds into the (R)-1-amino-2-(4- hydroxyphenyl)-ethylphosphonic acid moiety of compound K-26 suggests a new mechanism of biosynthesis of phosphonate functionality in natural products.

Original languageEnglish (US)
Pages (from-to)2763-2765
Number of pages3
JournalOrganic Letters
Volume7
Issue number13
DOIs
StatePublished - Dec 1 2005

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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