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

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

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

40 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 language	English (US)
Pages (from-to)	2763-2765
Number of pages	3
Journal	Organic Letters
Volume	7
Issue number	13
DOIs	https://doi.org/10.1021/ol051091d
State	Published - Dec 1 2005

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Biosynthetic origins of C-P bond containing tripeptide K-26",

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.",

author = "Ioanna Ntai and Manier, {M. Lisa} and Hachey, {David L.} and Bachmann, {Brian O.}",

year = "2005",

month = dec,

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doi = "10.1021/ol051091d",

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journal = "Organic Letters",

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T1 - Biosynthetic origins of C-P bond containing tripeptide K-26

AU - Ntai, Ioanna

AU - Manier, M. Lisa

AU - Hachey, David L.

AU - Bachmann, Brian O.

PY - 2005/12/1

Y1 - 2005/12/1

N2 - (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.

AB - (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.

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JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

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

Abstract

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