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ChemInform Abstract: Chemical and Enzymatic Diastereoselective Cleavage of β-D-Galactopyranosylsulfoxides.

✍ Scribed by N. KHIAR; I. ALONSO; N. RODRIGUEZ; A. FERNANDEZ-MAYORALAS; J. JIMENEZ-BARBERO; O. NIETO; F. CANO; C. FOCES-FOCES; M. MARTIN-LOMAS

Publisher
John Wiley and Sons
Year
2010
Weight
35 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis

Chemical and Enzymatic Diastereoselective Cleavage of β-D-Galactopyranosylsulfoxides.

-Several thio-β-D-galactopyranosides of type (I) undergo self-induced diastereoselective MCPBA-oxidation; however, only low to moderate diastereoselectivities of the sulfoxides (II) are obtained. Enzymatic hydrolysis of a diastereomeric mixture of unprotected phenylsulfinylβ-D-galactopyranosides (III) results in complete conversion of the (7'S) isomer, whereas the minor isomer remains unchanged. Acidic hydrolysis of (III) in aqueous triflic acid reveals (7'S)-(III) being twice more reactive than its epimer. -

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