Module 11 : Enzyme-Catalyzed Asymmetric Reactions

Lecture 37: Acylation and Hydrolytic Reactions

11.2.3  Hydantoin Hydrolysis

 

Hydantoinases and carbamoylases hydrolyses racemic hydantoins to give optically pure α -amino acids (Scheme 12). In the beginning, the hydantoinase catalyzes the hydrolytic ring opening of the hydantoin to give an N -carbamoyl amino acid that proceeds cleavage to give the desired α -amino acid.

Scheme 12

11.2.4  Epoxide Hydrolysis

 

Hydrolysis of racemic epoxide using epoxide hydrolase proceeds with high enantioselectivity. For example, the resolution of aliphatic epoxide having functional group can be accomplished using Methylobacterium sp. with good enantioselectivity (Scheme 13).

Scheme 13