Hydantoin → Alloisoleucine, D-
Reaction equation
N1CC(=O)NC1=O.N1CC(=O)NC1=O.[NH2:15][C@H:16]([C:21]([OH:23])=[O:22])[C@H:17]([CH2:19][CH3:20])[CH3:18].C(N[C@@H](C(O)=O)[C@H](CC)C)(=O)N>>[NH2:15][C@@H:16]([C:21]([OH:23])=[O:22])[C@H:17]([CH2:19][CH3:20])[CH3:18]Participants
4
Procedure
Preferably in the claimed method the contacting of the hydantoin with a D-hydantoinase is carried out under conditions permitting the simultaneous epimerization of the chiral center at C-5 of the hydantoin. As discussed further below, the simultaneous epimerization permits the reaction to be carried out to substantial completion so that L-isoleucine hydantoin is converted to N-carbamoyl-D-allo-isoleucine. The N-carbamoyl-D-allo-isoleucine is then decarbamoylated to produce D-allo-isoleucine.