Lyxose 5-deoxy-3-formyl

Streptose is the first branched-chain sugar to have been identified as a component of a biological compound produced by a microorganism. This dicarbonyl sugar is known only in its derivatives. The chemistry of streptose and streptomycin has been lucidly reviewed by Lemieux and Wolfrom.1 In this article, it was noted that streptose must be either 5-deoxy-3-C -formyl-L-ribose or 5-deoxy-3-C-formyl-L-lyxose. Since then, the presence of the latter configuration (XXXIV) has been definitely established by Wolfrom and DeWalt,66 who found that N-acetyltetrahydrostreptobi-... 

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. 

L-Streptose 5-deoxy-3-formyl-L-lyxose, a monosaccharide, 162.14, with a branehed carbon chain. In combination with 2-deoxy-2-methyIamino-L-glucose, L-S forms streptobiosamine, the disaccharide component of Streptomycin (see). l-S. is biosynthesized by rearrangement of an unbranched hexose. 

Streptobiose 2-Deoxy-2-methylamino-a-L-glucopyranosyl-(1 2)-5-deoxy-3-C-formyl-L-lyxose... 

---