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

Ioanna Ntai; M Lisa Manier; David L Hachey; Brian O Bachmann

doi:10.1021/ol051091d

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

Org Lett. 2005 Jun 23;7(13):2763-5. doi: 10.1021/ol051091d.

Authors

Ioanna Ntai¹, M Lisa Manier, David L Hachey, Brian O Bachmann

Affiliation

¹ Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235-1822, USA.

PMID: 15957941
DOI: 10.1021/ol051091d

Abstract

[reaction: see text] 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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Actinomyces / chemistry*
Molecular Structure
Oligopeptides* / biosynthesis
Oligopeptides* / chemical synthesis
Oligopeptides* / chemistry
Phosphinic Acids / chemistry*
Spectrometry, Mass, Electrospray Ionization

Substances

Oligopeptides
Phosphinic Acids
tripeptide K-26