✍ Scribed by Benoît Joseph; Patrick Rollin
No coin nor oath required. For personal study only.
Many biologically important molecules involve two sugar units connected through one atom (e.g., the acetal function in disaccharides) or several atoms (e.g., the phosphoric ester in dinucleotides). Replacing these naturally-occurring bridges by other sequences results in structural analogues, or isosteres of natural compounds, which may behave as enzyme inhibitors [ 1 ]. S-, N-, and C-Disaccharides are already known [ 2,.-5 ] whereas pseudodinucleotides [ 6] and pseudodisaccharides displaying various functional bridges such as disul.. fide [7], hydrazine [8], carbonate [9] and xanthate [10], carbamate [11] and thiocarbamate [ 12], thiourea [ 13], etc., have also been synthesized. Surprisingly, almost no examples of a catboxylate ester function bridging two sugar units have been reported, with the exception of Ogawa's serendipitous oxidative transformation [ 14] or the sporadically observed Tischenko-type side reactions [ 15 ]. In connection with our recent studies on the synthesis of artificial glucosinolates [ 16], a new class of pseudodisaccharides has been synthesized, in which the two sugar units are linked by a (Z)-thiohydroximate function (Scheme 1). N .o t Scheme 1.
📜 SIMILAR VOLUMES
## Abstract For Abstract see ChemInform Abstract in Full Text.