Fluorinated and deoxygenated glycosides as mechanistic probes of Escherichia coli (lacZ) β-galactosidase. By use of the slow substrate 2,4-dinitrophenyl-2-deoxy-2-fluoro-β-D-galactopyranoside, a glycosyl enzyme intermediate has been trapped on the enzyme. Glu-268 was identified as the catalytic nucleophile of human lysosomal β-galactosidase precursor.
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