Streptomyces fumanus, intramurally coded as culture LL-F42248, produces
a series of pyrrolomycins including dioxapyrrolomycin (1) as the
principal component. Our biosynthetic studies revealed that feeding
labeled acetate to growing cultures of S. fumanus yielded pyrrolomycins
labeled in the phenyl ring only. When l-methyl-13Cmethionine was
fed, the labeled carbon atom was found in the methoxy group of pyrrolomycins
H-J and in the methylenedioxy bridge of dioxapyrrolomycin. A Na15NO3-enriched
medium was employed to produce 15N-labeled pyrrolomycins in which
both nitrogen atoms were highly enriched, whereas feeding of 15N-labeled
l-proline furnished pyrrolomycins labeled in the pyrrole moiety.
Thus, S. fumanus elaborates the pyrrolomycin skeleton from proline
and a polyketide precursor. Since the organism readily converted
13C- or 15N-labeled pyrrolomycin C, G, or H into the correspondingly
labeled dioxapyrrolomycin, these minor pyrrolomycins are actually
precursors of the ultimate product, dioxapyrrolomycin.
%0 Journal Article
%1 citeulike:819621
%A Charan, R. D.
%A Schlingmann, G.
%A Bernan, V. S.
%A Feng, X.
%A Carter, G. T.
%C Chemical and Screening Sciences, Wyeth Research, 401 N. Middletown
Road, Pearl River, New York 10965, USA.
%D 2006
%J J Nat Prod
%K natural-products nitro-compounds biosynthesis
%N 1
%P 29--33
%R 10.1021/np0503404
%T Dioxapyrrolomycin biosynthesis in Streptomyces fumanus.
%U http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=16441063
%V 69
%X Streptomyces fumanus, intramurally coded as culture LL-F42248, produces
a series of pyrrolomycins including dioxapyrrolomycin (1) as the
principal component. Our biosynthetic studies revealed that feeding
labeled acetate to growing cultures of S. fumanus yielded pyrrolomycins
labeled in the phenyl ring only. When l-methyl-13Cmethionine was
fed, the labeled carbon atom was found in the methoxy group of pyrrolomycins
H-J and in the methylenedioxy bridge of dioxapyrrolomycin. A Na15NO3-enriched
medium was employed to produce 15N-labeled pyrrolomycins in which
both nitrogen atoms were highly enriched, whereas feeding of 15N-labeled
l-proline furnished pyrrolomycins labeled in the pyrrole moiety.
Thus, S. fumanus elaborates the pyrrolomycin skeleton from proline
and a polyketide precursor. Since the organism readily converted
13C- or 15N-labeled pyrrolomycin C, G, or H into the correspondingly
labeled dioxapyrrolomycin, these minor pyrrolomycins are actually
precursors of the ultimate product, dioxapyrrolomycin.
@article{citeulike:819621,
abstract = {Streptomyces fumanus, intramurally coded as culture LL-F42248, produces
a series of pyrrolomycins including dioxapyrrolomycin (1) as the
principal component. Our biosynthetic studies revealed that feeding
labeled acetate to growing cultures of S. fumanus yielded pyrrolomycins
labeled in the phenyl ring only. When l-[methyl-13C]methionine was
fed, the labeled carbon atom was found in the methoxy group of pyrrolomycins
H-J and in the methylenedioxy bridge of dioxapyrrolomycin. A Na15NO3-enriched
medium was employed to produce 15N-labeled pyrrolomycins in which
both nitrogen atoms were highly enriched, whereas feeding of 15N-labeled
l-proline furnished pyrrolomycins labeled in the pyrrole moiety.
Thus, S. fumanus elaborates the pyrrolomycin skeleton from proline
and a polyketide precursor. Since the organism readily converted
13C- or 15N-labeled pyrrolomycin C, G, or H into the correspondingly
labeled dioxapyrrolomycin, these minor pyrrolomycins are actually
precursors of the ultimate product, dioxapyrrolomycin.},
added-at = {2007-02-02T11:54:15.000+0100},
address = {Chemical and Screening Sciences, Wyeth Research, 401 N. Middletown
Road, Pearl River, New York 10965, USA.},
author = {Charan, R. D. and Schlingmann, G. and Bernan, V. S. and Feng, X. and Carter, G. T.},
biburl = {https://www.bibsonomy.org/bibtex/2602fe58da3cfcad7ccb70745263b1b43/robert},
citeulike-article-id = {819621},
doi = {10.1021/np0503404},
interhash = {c4c691797b2c9f0bf461d152ab09a7ae},
intrahash = {602fe58da3cfcad7ccb70745263b1b43},
issn = {0163-3864},
journal = {J Nat Prod},
keywords = {natural-products nitro-compounds biosynthesis},
month = {January},
number = 1,
pages = {29--33},
priority = {2},
timestamp = {2007-02-02T11:54:15.000+0100},
title = {Dioxapyrrolomycin biosynthesis in Streptomyces fumanus.},
url = {http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve\&db=pubmed\&dopt=Abstract\&list_uids=16441063},
volume = 69,
year = 2006
}