Abstract
Several 4-deoxy analogs of methyl β- D-galactopyranoside are oxidized by D-galactose oxidase. The rates associated with their various, axially attached 4-substituents follow the sequence OH>NH 2>F⪢>Cl> H; these differences are attributed mainly to variations in K m . Other 4-deoxy analogs, namely, the 4-azido-4-deoxy, 4-bromo-4-deoxy-, 4-deoxy-4-iodo, and 4-thio derivatives were found to be inactive. These observations indicate that the axial 4-hydroxyl group of D-galactopyranose does not play a hydrogen-bonding role primarily, but constitutes a substituent of a size optimal for interaction with the enzyme.
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