Streptamine biosynthesis

Aminoglycosides. Antibiotics in the aminoglycoside group characteristically contain amino sugars and deoxystreptamine or streptamine, This family of antibiotics has frequently been referred to as aminocyclitol aminoglycosides. Representative members are streptomycin, neomycin, kanamycin, gentamicin, tobramycin, and amikacin. These antibiotics all inhibit protein biosynthesis,... 

Scheme 12. 5-Deoxygenation during the biosynthesis of 2-deoxystreptamine (27 the core moiety of neomycin 25, streptamine 26 is its analog in streptomycin 24) through transamination of the intermediate 2-deoxy-scyl/o-inosose (28). Note that C-5 of glucose becomes C-3 of 26 and 27...

Some mutants have been used during biosynthesis to incorporate modified deoxystreptamine derivatives. In such so called mutasynthesis or mutational biosynthesis new aminoglycoside antibiotics can be prepared. A series of analogues of 2-deoxystreptamine has been used in different 2-deoxystreptamine-negative mutants to determine whether they are converted to antibiotics. Only limited substitution at the 2-position (streptamine, epi-streptamine, 1-N-methyldeoxystrepta-... 

Walker JB, Skorvaga M, Streptomycin biosynthesis and metabolism. Phosphate transfer from dibydrostreptomycin 6-phosphate to inosamines, streptamine. and 2-deoxystreptamine. J Biol Chem 1973 248 2435-2440. 

The loss of the C-4 hydrogen atom of D-glucose in the biosynthesis of the deoxy streptamine ring of neomycin has been taken to... 

Walker, M. S., and J. B. Walker Enzymatic studies on the biosynthesis of streptomycin Transamidination of inosamine and streptamine derivatives. J. Biol. Chem. 241, 1262 (1966). 

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