Studies on the biosynthesis of the antibiotic crisamicin A and carbon-13 magnetic resonance assignments

Richard A. Nelson; Lloyd E. McDaniel; Carl P. Schaffner; Joseph A. Pope; Ramesh C. Pandey; Richard L. Beveridge; Phil H. Hoops; Frank Jordan

doi:10.7164/antibiotics.41.1659

Studies on the biosynthesis of the antibiotic crisamicin A and carbon-13 magnetic resonance assignments

Richard A. Nelson, Lloyd E. McDaniel, Carl P. Schaffner, Joseph A. Pope, Ramesh C. Pandey, Richard L. Beveridge, Phil H. Hoops, Frank Jordan

Rutgers Newark, Chemistry

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

8 Scopus citations

Abstract

The biosynthesis of crisamicin A, a novel dimeric isochromanequinone antibiotic from Micromonospora purpureochromogenes subsp. halotolerans has been investigated by [1-¹³C] and [2-¹³C] labeled acetate precursor feeding experiments. Analysis of the proton noise decoupled and off resonance ¹³C NMR spectra of ¹³C enriched and unenriched crisamicin A and their acetate derivatives indicated the biosynthesis via the polyketide pathway, as expected. Further analysis of the enriched spectra allowed the complete assignment of the carbon signals. Of particular interest was the establishment of the linkage between the two monomeric halves of the molecule and determination of the location of the phenolic hydroxyls.

Original language	English (US)
Pages (from-to)	1659-1667
Number of pages	9
Journal	The Journal of Antibiotics
Volume	41
Issue number	11
DOIs	https://doi.org/10.7164/antibiotics.41.1659
State	Published - 1988

All Science Journal Classification (ASJC) codes

Pharmacology
Drug Discovery

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title = "Studies on the biosynthesis of the antibiotic crisamicin A and carbon-13 magnetic resonance assignments",

abstract = "The biosynthesis of crisamicin A, a novel dimeric isochromanequinone antibiotic from Micromonospora purpureochromogenes subsp. halotolerans has been investigated by [1-13C] and [2-13C] labeled acetate precursor feeding experiments. Analysis of the proton noise decoupled and off resonance 13C NMR spectra of 13C enriched and unenriched crisamicin A and their acetate derivatives indicated the biosynthesis via the polyketide pathway, as expected. Further analysis of the enriched spectra allowed the complete assignment of the carbon signals. Of particular interest was the establishment of the linkage between the two monomeric halves of the molecule and determination of the location of the phenolic hydroxyls.",

author = "Nelson, {Richard A.} and McDaniel, {Lloyd E.} and Schaffner, {Carl P.} and Pope, {Joseph A.} and Pandey, {Ramesh C.} and Beveridge, {Richard L.} and Hoops, {Phil H.} and Frank Jordan",

year = "1988",

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T1 - Studies on the biosynthesis of the antibiotic crisamicin A and carbon-13 magnetic resonance assignments

AU - Nelson, Richard A.

AU - McDaniel, Lloyd E.

AU - Schaffner, Carl P.

AU - Pope, Joseph A.

AU - Pandey, Ramesh C.

AU - Beveridge, Richard L.

AU - Hoops, Phil H.

AU - Jordan, Frank

PY - 1988

Y1 - 1988

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AB - The biosynthesis of crisamicin A, a novel dimeric isochromanequinone antibiotic from Micromonospora purpureochromogenes subsp. halotolerans has been investigated by [1-13C] and [2-13C] labeled acetate precursor feeding experiments. Analysis of the proton noise decoupled and off resonance 13C NMR spectra of 13C enriched and unenriched crisamicin A and their acetate derivatives indicated the biosynthesis via the polyketide pathway, as expected. Further analysis of the enriched spectra allowed the complete assignment of the carbon signals. Of particular interest was the establishment of the linkage between the two monomeric halves of the molecule and determination of the location of the phenolic hydroxyls.

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Studies on the biosynthesis of the antibiotic crisamicin A and carbon-13 magnetic resonance assignments

Abstract

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