Chemical and enzymatic diastereoselective cleavage of β-D galactopyranosylsulfoxides

Article abstract of DOI:10.1016/S0040-4039(97)10164-2

The self induced diastereoselective oxidation of several thio-β-D- galactopyranosides to the corresponding sulfoxides, has been shown to occur in high yield. Up to 74% diastereomeric excess could be obtained depending on the structure and the conformation of the starting thioglycoside. Rs and Ss Phenylsulfinyl-β-D-galactopyranosides have been obtained in optically pure forms, their chemical as well as enzymatic hydrolysis with triflic acid and with β-galactosidase have been shown to proceed diastereoselectively, the structure of the sulfoxide 4'S with the S configuration at the sulfinyl sulfur has been determined by X-ray analysis.