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 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.
Zhou
Z Y
ZY
Department of Biotechnology, Faculty of Engineering, Osaka University, Japan.
Sakuda
S
S
Kinoshita
M
M
Yamada
Y
Y
D000117:Acetylglucosamine / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000494:pharmacology; D002240:Carbohydrate Sequence; D002688:Chitinases / Q000037:antagonists & inhibitors*; D002851:Chromatography, High Pressure Liquid; D007306:Insecticides; D008969:Molecular Sequence Data; D013302:Streptomyces / Q000737:chemistry*; D014312:Trisaccharides / Q000096:biosynthesis* / Q000494:pharmacology
D007306:Insecticides; D014312:Trisaccharides; C054851:allosamidin; D002688:Chitinases; D000117:Acetylglucosamine