Aminosugar antibiotics, synthesis

There are several reports in the literature that suggest that antibiotic synthesis may be repressed by ammonia and other rapidly utilized nitrogen sources (96). However, there are no detailed studies on the possible nitrogen regulation of the biosynthesis of mycosamine or other aminosugars of polyenes. 

A synthesis of 6-deoxy-6-hydroxyamino- -D-glucopyranoside from the corresponding 6-aminosugar by the sequence of oxidation with hydrogen peroxide - sodium tungstate to the oxime followed by cyanoborohydride reduction was copied in a synthesis of the pseudo-trisaccharides 6 -N-hydroxykanamycin A and 6 -N-hydroxydibekacin from the corresponding parent antibiotics, but the products were... 

A number of papers have described routes from carbohydrates to hydroxyl-ated aminoacids. The azide (78), derived from L-arabinose, was converted, via the 4,5-azirldine. into polyoxamlc acid (79), a constituent of the polyoxin class of antibiotics.The aminosugar derivative (80), an intermediate in Horton s daunosamine synthesis, can be transformed (Scheme 19) into (81), and hence into the lactone (82), which is a protected form of the hydrojqrlated 3-amino-acid found in the antiulcerogenic compound AI-77-B the regiochemistry in the reductive opening of the acetal is unexpected. 72 o-Glucose has been converted... 

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