Sub-unit assembly in the biosynthesis of neomycin. The synthesis of 5-O-beta-D-ribofuranosyl and 4-O-beta-D-ribofuranosyl-2,6-dideoxystreptamines. 1978

C J Pearce, and M Akhtar, and J E Barnett, and D Mercier, and A M Sepulchre, and S D Gero

The preparation of the deoxy- analogues of two pseudodisaccharide fragments of neomycin, 5-O-beta-D-ribofuranosyl-2,6-dideoxy-streptamine and 6-deoxyneamine is described. When added to the growth medium of a deoxystreptamine-idiotroph of Streptomyces rimosus forma paromomycinus only the latter was incorporated into antibiotic, suggesting an obligatory order for the assembly of sub-units. 4-O-beta-D-Ribofuranosyl-2,6-dideoxystreptamine was also prepared. When added to the growth medium of a deoxystreptamine-idiotroph of Streptomyces fradiae it was converted into the 6-deoxyneomycins, apparently after hydrolysis to 2,6-dideoxystreptamine. The structure of the protected derivatives of the ribofuranosyl 2,6-dideoxystreptamines, potentially useful intermediates for the synthesis of novel antibiotics, was shown by using 15C NMR spectroscopy.

UI MeSH Term Description Entries
D008722 Methods A series of steps taken in order to conduct research. Techniques,Methodological Studies,Methodological Study,Procedures,Studies, Methodological,Study, Methodological,Method,Procedure,Technique
D009355 Neomycin Aminoglycoside antibiotic complex produced by Streptomyces fradiae. It is composed of neomycins A, B, and C, and acts by inhibiting translation during protein synthesis. Fradiomycin Sulfate,Neomycin Palmitate,Neomycin Sulfate
D006595 Hexosamines AMINO SUGARS created by adding an amine group to a hexose sugar. Hexosamine
D013302 Streptomyces A genus of bacteria that form a nonfragmented aerial mycelium. Many species have been identified with some being pathogenic. This genus is responsible for producing a majority of the ANTI-BACTERIAL AGENTS of practical value.

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