The hydrolysis of glycosyl fluorides by glycosidases

1. alpha-d- and beta-d-Glucopyranosyl, alpha-d- and beta-d-galactopyranosyl, alpha-d-mannopyranosyl and alpha-d-xylopyranosyl fluorides were hydrolysed specifically by the respective glycosidases from several sources. 2. Use of specific inhibitors with a mixture of glycosidases from Helix pomatia intestinal juice showed that each glycosyl fluoride was hydrolysed only by the respective glycosidase. alpha-d-Glucopyranosidase and alpha-d-xylopyranosidase activities were shown to be due to different enzymes. 3. Partially purified enzyme preparations containing only one of the glycosidase activities hydrolysed only the corresponding glycosyl fluoride. 4. The configuration at C-1 of alpha-d-mannopyranosyl fluoride was confirmed since it was hydrolysed by an alpha-d-mannosidase preparation that contained no detectable beta-d-mannosidase activity. 5. An attempt to prepare o-nitrophenyl beta-d-mannopyranoside led only to o-nitrophenyl alpha-d-mannopyranoside.