Kinamycin Biosynthesis. Synthesis, Isolation, and Incorporation of Stealthin C, an Aminobenzo[b]fluorene

A new intermediate in the biosynthesis of the benzo[b]fluorene antibiotic, kinamycin D, has been identified. 11-Amino-4,5,9-trihydroxy-2-methyl-10H-benzo[b]fluoren-10-one was synthesized and shown to be present in extracts of Streptomyces murayamaensis fermentations. A deuterated sample was prepared...

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Published inJournal of organic chemistry Vol. 62; no. 2; pp. 320 - 324
Main Authors Gould, Steven J, Melville, Chris R, Cone, Martha C, Chen, Jiong, Carney, John R
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 24.01.1997
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ANTIBIOTICS
ORIGIN
VALANIMYCIN
PRODUCTS
STREPTOMYCES-MURAYAMAENSIS
BIOLOGICAL PROPERTIES
ELAIOMYCIN
ACETATE
BOND
PHENANTHROVIRIDIN AGLYCON
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Summary:A new intermediate in the biosynthesis of the benzo[b]fluorene antibiotic, kinamycin D, has been identified. 11-Amino-4,5,9-trihydroxy-2-methyl-10H-benzo[b]fluoren-10-one was synthesized and shown to be present in extracts of Streptomyces murayamaensis fermentations. A deuterated sample was prepared and shown to be specifically incorporated into kinamycin D. This new intermediate, now named stealthin C, is also the probable hydroxylation substrate for the biosynthesis of stealthin A by S. viridochromogenes.
Bibliography:istex:723C2692DD4FFCE8E5C7C9903ED878B94C584A84
Abstract published in Advance ACS Abstracts, December 15, 1996.
ark:/67375/TPS-J34N6D36-6
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo961486y