L-Isoleucine → Alloisoleucine, D-

Reaction equation

[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4].N1CC(=O)NC1=O.N1CC(=O)NC1=O.N[C@@H](C(O)=O)[C@H](CC)C.C(N[C@@H](C(O)=O)[C@H](CC)C)(=O)N>>[NH2:1][C@@H:2]([C:7]([OH:9])=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4]

Participants

Reactant 4

HCID 6306L-Isoleucine

HCID 10006Hydantoin2×

HCID 854211HCID 854211, compound2×

HCID 86590268HCID 86590268, compound

Product 1

HCID 94206Alloisoleucine, D-

Procedure

A method for producing D-allo-isoleucine is provided. The method comprises converting L-isoleucine to the corresponding hydantoin. A mixture containing the hydantoin is contacted with a D-hydantoinase to stereoselectively hydrolyze any D-allo-isoleucine hydantoin in the mixture to the corresponding N-carbamoyl-D-allo-isoleucine. The N-carbamoyl-D-allo-isoleucine is decarbamoylated to produce D-allo-isoleucine. Preferably 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.