title: Biosynthetic origins of C-P bond containing tripeptide K-26.
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.
authors.affiliation: Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235-1822, USA.
authors.forename: Ioanna
authors.initials: I
authors.lastname: Ntai
authors.forename: M Lisa
authors.initials: ML
authors.lastname: Manier
authors.forename: David L
authors.initials: DL
authors.lastname: Hachey
authors.forename: Brian O
authors.initials: BO
authors.lastname: Bachmann
mesh_terms: 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
chemical_list: D009842:Oligopeptides; D010721:Phosphinic Acids; C508953:tripeptide K-26