American Chemical Society
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Biosynthetic Origins of C−P Bond Containing Tripeptide K-26

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journal contribution
posted on 2005-06-23, 00:00 authored by Ioanna Ntai, M. Lisa Manier, David L. Hachey, Brian O. Bachmann
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.