3 "-Deoxy dihydrostreptomycin

The earliest known member of this group was streptose, which is present in streptomycin. Its structure was shown to be that of 5-deoxy-3-C-formyl-L-lyxose (57). Both a hydroxylated and a reduced form of streptose have been found in variants of streptomycin produced by other Streptomyces sp. The former, 5-hydroxystreptose (3-formyl-L-lyxose) (58), occurs in hydroxystreptomycin and the latter, dihydrostreptose Q5-deoxy-3-(hydroxymethyl)-L-lyxose] (59), in dihydrostreptomycin. 

HQNO (1) and A -deoxy-HQNO (2) have weak activity against Gram-positive bacteria, 1 inhibits the mitochondrial respiratory chain in the cytochrome bCj complex, 5-lipoxygenase, and is an antagonist to the antibacterial activity of dihydrostreptomycin. 

Deoxydihydrosteptomycin has been synthesized from dihydrostreptomycin by a standard tosyloxy — chloro -> deoxy... 

Several Streptomyces strains or species produce compounds closely related structurally to streptomycin. These structural modifications involve the L-streptose and streptidine moieties. Those involving only modifications of the streptose moiety are dihydrostreptomycin and hydroxystreptomycin. Dihydrostreptomycin contains L-dihydrostreptose (3-C-hydroxymethyl-5-deoxy-L-lyxofuranose) in place of streptose (Bartz et at., 1946 Tatsuoka et at., 1964) (Fig. 2). 

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