Three topics of recent achievements in the application of enzyme- and micro
organism-catalyzed reactions to organic synthesis are focused. 1) Asymmetri
c synthesis and enantiomeric resolution, such as yeast-catalyzed asymmetric
reduction of a carbonyl group and hydrolytic enzyme - catalyzed enantiosel
ective hydrolysis of esters and transesterification are described. Special
emphasis is laid on the enzyme-catalyzed preparation of alpha-hydroxy acids
in enantiomerically enriched forms. Examples of enzyme-catalyzed asymmetri
c C-C bond formation are shortly commented. 2) The advantage of enzymatic h
ydrolysis of nitriles, amides, and esters are introduced, as the examples o
f the transformation of functional groups under mild condition. 3) The comp
lementary use of chemical and enzymatic reaction in the total scheme is sho
wn, in our synthesis of pyrenophorin and N-glycolylneuraminic acid.