Location of a proton-donating group at the re-face of a β- d-galactosidase-bound, diastereotopic substrate

( Z)-3,7-Anhydro-1,2-dideoxy-2-deuterio- d- galacto-oct-2-enitol ( 1) was used as a diastereotopic probe, in order to elucidate the stereochemistry of protonation by β- d-galactosidase. Compound 1 can be converted by the enzyme into 1,2-dideoxy-2-deuterio- d- galacto-3-octulopyranose ( 2), which was...

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Published in:Carbohydrate research 1983-01, Vol.113 (1), p.93-99
Main Authors: Lehmann, Jochen, Schlesselmann, Peter
Format: Article
Language:English
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Summary:( Z)-3,7-Anhydro-1,2-dideoxy-2-deuterio- d- galacto-oct-2-enitol ( 1) was used as a diastereotopic probe, in order to elucidate the stereochemistry of protonation by β- d-galactosidase. Compound 1 can be converted by the enzyme into 1,2-dideoxy-2-deuterio- d- galacto-3-octulopyranose ( 2), which was submitted to periodate degradation. Propanoic acid derived from C-1, 2, and 3 of 2 has the ( S) configuration, which proved the enzymic protonation of 1 to have taken place exclusively from the re-face.
ISSN:0008-6215
1873-426X
DOI:10.1016/0008-6215(83)88221-4