The transmannosylation activity of beta-mannosidase from snail and beta-galactosidase from Aspergillus oryzae was used for the synthesis of methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 1-hexyl, cyclohexyl, and 1-octyl beta-D-mannopyranosides (3a-i), respectively. The regioisomeric specificities and wide substrate acceptance of this galactosidase are demonstrated. Thus, 4-nitrophenyl 4-O-(alpha-D-glucopyranosyl)-beta-D-glucopyranoside (6), 4-nitrophenyl 2-O-(O-D-glucopyranosyl)-beta-D-glucopyranoside (7), 4-nitrophenyl 2-deoxy-2N-acetyl-6-O-(2-deoxy-2-N-acetyl-beta-D-glucopyranosyl)-beta-D-glucopyranoside (8), 4-nitrophenyl 3-O-(beta-D-mannopyranosyl)-alpha-D-mannopyranoside (9), and 4-nitrophenyl 4-O-(beta-D-mannopyranosyl)-beta-D-mannopyranoside (10) were prepared by chemoenzymatic self-transfer reaction.