Biosynthetic origins of C-P bond containing tripeptide K-26.
[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.
Ntai
Ioanna
I
Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235-1822, USA.
Manier
M Lisa
ML
Hachey
David L
DL
Bachmann
Brian O
BO
D000190:Actinomyces / Q000737:chemistry*; D015394:Molecular Structure; D009842:Oligopeptides / Q000096:biosynthesis / Q000138:chemical synthesis / Q000737:chemistry; D010721:Phosphinic Acids / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
D009842:Oligopeptides; D010721:Phosphinic Acids; C508953:tripeptide K-26