BIOSYNTHETIC STUDIES OF ALLOSAMIDIN: 2. ISOLATION OF DIDEMETHYLALLOSAMIDIN, AND CONVERSION EXPERIMENTS OF 14C-LABELED DEMETHYLALLOSAMIDIN, DIDEMETHYLALLOSAMIDIN AND THEIR RELATED COMPOUNDS

A new allosamidin analog, termed didemethylallosamidin (3), was isolated from the mycelia of Streptomyces sp. AJ 9463 which is a producer of allosamidin (1) and demethylallosamidin (2). 14C-Labeled 1, 2 and 3 as well as their related compounds, 4, 5, and 6, were prepared to investigate the biosynthe...

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Bibliographic Details
Published in:Journal of antibiotics 1993/10/25, Vol.46(10), pp.1582-1588
Main Authors: ZHOU, ZE-YANG, SAKUDA, SHOHEI, KINOSHITA, MASAYOSHI, YAMADA, YASUHIRO
Format: Article
Language:English
Subjects:
Acetylglucosamine - analogs & derivatives
Acetylglucosamine - biosynthesis
Acetylglucosamine - pharmacology
Carbohydrate Sequence
Chitinases - antagonists & inhibitors
Chromatography, High Pressure Liquid
Insecticides
Molecular Sequence Data
Streptomyces - chemistry
Trisaccharides - biosynthesis
Trisaccharides - pharmacology
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Summary:A new allosamidin analog, termed didemethylallosamidin (3), was isolated from the mycelia of Streptomyces sp. AJ 9463 which is a producer of allosamidin (1) and demethylallosamidin (2). 14C-Labeled 1, 2 and 3 as well as their related compounds, 4, 5, and 6, were prepared to investigate the biosynthesis of 1. Conversion experiments with the labeled allosamidins revealed that 2 was a precursor of 1, but 3 was not incorporated. This suggests that the first N-methyl group is introduced before the cyclization of the aminooxazoline ring during the biosynthesis of 1. Although none of the compounds 4, 5, and 6 were converted to 1, the production of 1 was inhibited by the addition of 4.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.46.1582