Structure elucidation of an intermediate of 2-deoxystreptamine biosynthesis.
نویسندگان
چکیده
The structure of a 2-deoxystreptamine (DOS) precursor named S-11-P, which was isolated by using a DOS negative mutant derived from a xylostasin-producing strain of Bacillus circulans B15M, has been elucidated as (1 L)-1,3,5/2,4,-5-aminocyclohexanetetrol by comparison with an authentic specimen, which was synthesized from kanamycin A.
منابع مشابه
Isolation of an intermediate of 2-deoxystreptamine biosynthesis from a mutant of Bacillus circulans.
Eight 2-deoxystreptamine-negative (DOS-) mutants were isolated from various strains of Bacillus circulans, normally producing butirosin, xylostasin and ribostamycin. These mutants were classified into two groups (converter and secretor) by the simple method of cosynthesis using agar plate culture. One of the cosynthetic pairs, strain S-11, an intermediate of DOS biosynthesis, S-11-P, was isolat...
متن کاملBiochemical studies on 2-deoxy-scyllo-inosose, an early intermediate in the biosynthesis of 2-deoxystreptamine. I. Chemical synthesis of 2-deoxy-scyllo-inosose and [2,2-2H2]-2-deoxy-scyllo-inosose.
A practical preparative method for 2-deoxy-scyllo-inosose, the earliest key intermediate leading to 2-deoxystreptamine, was devised as a prerequisite to more detailed biochemical studies on the biosynthesis of 2-deoxystreptamine. [2,2-2H2]-2-Deoxy-scyllo-inosose was also synthesized through a modified Ferrier reaction.
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step in the biosynthesis of 1 is the formation of the precursor, 2-deoxy-scy//0-inosose (2), from D-glucose (3) via the intramolecular C-C bond formation between C-l and C-6.li2) The transformation of 3 into 2 was proposed by us to involve a multi-step mechanismas shownin Scheme1, the chemistry of which was suggested to be similar to the dehydroquinate synthase in the shikimate pathway,3'4* and...
متن کاملProduction of a new aminoglycoside antibiotic by a mutant of Bacillus circulans.
A new aminoglycoside antibiotic, S-11-A, was isolated from the fermentation broth of the 2-deoxystreptamine negative (DOS-) mutant of Bacillus circulans S-11. The structure of S-11-A was elucidated as 1-deamino-1-hydroxyxylostasin, which contains an intermediate of DOS biosynthesis (S-11-P) and has resistance to some aminoglycoside-inactivating enzymes. This is the first finding of antibiotic p...
متن کاملNeomycin biosynthesis: the incorporation of D-6-deoxy-glucose derivatives and variously labelled glucose into the 2-deoxystreptamine ring. Postulated involvement of 2-deoxyinosose synthase in the biosynthesis.
D-[6-3H3]6-Deoxy-5-ketoglucose (10) and D-[5,6-3H2]6-deoxyglucose (11) were incorporated into neomycins B and C using a growing culture of Streptomyces fradiae. D-[6-3H]6-Deoxy-5-ketoglucose was incorporated into neomycin, as efficiently as the well established precursor D-glucose, and was found to label exclusively the 2-deoxystreptamine ring of the antibiotic. The results strengthened the pre...
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ورودعنوان ژورنال:
- The Journal of antibiotics
دوره 33 8 شماره
صفحات -
تاریخ انتشار 1980