SUGAR MIMICS FROM SUGAR LACTONES

The potential of carbohydrate mimics which incorporate an a-amino acid moiety at the anomeric position of the sugar is illustrated by the sy nthesis of both furanose and pyranose analogues of L-rhamnose in a stu dy related to inhibition of the biosynthesis of mycobacterial cell wal ls. Some amino acid analogues of glucopyranose are inhibitors of glyco gen phosphorylase ard may provide an approach to the treatment of late -onset diabetes; bicyclic lactone intermediates provide relatively eas y access to both open chain and spiro derivatives of glucose in which both nitrogen and carbonyl functions are present at the anomeric posit ion, and in which the anomeric configuration is defined. Other glucose analogues were found to be inhibitors of glucokinase and glucose-6-ph osphatase; such materials may allow the investigation of metabolic con trol by the levels of sugar phosphates.