Biochemical Studies on 2-deoxy-sctllo-inosose, an Early Intermediate in the Biosynthesis of 2-deoxystreptamine Iv. a Clue to the Similarity of 2-deoxy-sc7ll0-inosose Synthase to Dehydroquinate Synthase
نویسنده
چکیده
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 an enzyme responsible of the intramolecular
منابع مشابه
Biochemical 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.
متن کاملMolecular cloning of the gene for the key carbocycle-forming enzyme in the biosynthesis of 2-deoxystreptamine-containing aminocyclitol antibiotics and its comparison with dehydroquinate synthase.
The 2-deoxystreptamine aglycon is a common structural feature found in aminocyclitol antibiotics including neomycin, kanamycin, tobramycin, gentamicin, sisomicin, butirosin and ribostamycin. A key enzyme involved in the biosynthesis of the 2-deoxystreptamine moiety is 2-deoxy-scyllo-inosose (DOI) synthase which catalyses the carbocycle formation from D-glucose-6-phosphate to 2-deoxy-scyllo-inos...
متن کاملSignificance of the 20-kDa subunit of heterodimeric 2-deoxy-scyllo-inosose synthase for the biosynthesis of butirosin antibiotics in Bacillus circulans.
A gene (btrC2) encoding the 20-kDa subunit of 2-deoxy-scyllo-inosose (DOI) synthase, a key enzyme in the biosynthesis of 2-deoxystreptamine, was identified from the butirosin-producer Bacillus circulans by reverse genetics. The deduced amino acid sequence of BtrC2 closely resembled that of YaaE of B. subtilis, but the function of the latter has not been known to date. Instead, BtrC2 appeared to...
متن کاملBiosynthesis of butirosins. II. Biosynthetic pathway of butirosins elucidated from cosynthesis and feeding experiments.
By cosynthetic studies, nine butirosin-non-producing blocked mutants of Bacillus circulans were classified into 7 groups (A to F and exceptional groups), based on their complementation patterns. Except for two strains of group A, mutant strains were all neamine-requiring idiotrophs. Mutants of group A produced xylostasin and ribostamycin and a mutant of group B accumulated 2-deoxystreptamine (D...
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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تاریخ انتشار 2006