Disaccharide Mimetics by Enzymatic Tandem Aldol Additions

摘要

The increasing amount of detailed knowledge on the mode of action of complex oligosacchandes in biological recognition phenomena and the occurrence of longer chain sugars as the bioactive principle of compounds like the tunicamycms have placed the synthesis, of higher homologous sugars containing 8- 1 3 carbons and their derivative- in the focus of modern carbohydrate chemistry. Of particular interest are C-disac chandes, as nonhydrolyzing antimetaholites. that is. potential inhibitors of ghcoside-proccssing enzymes. Classical svnthetic strategies- iterative chain elongation or convergent block condensations on the basis of available pentoses or hex-oses—require the free, unmasked carbonyl group of the sugar-and thus intensive protecting group manipulations. Limited availability or reactivity of suitably configurated precursors from the "chiral pool" are obvious further restrictions.