Hydantoin → D-Alloisoleucine

HRID 2416156Notes

Reaction equation

HRID 2416156 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

Reactant 3

HCID 10006Hydantoin2×HCID 854211HCID 854211, compound2×HCID 69816793HCID 69816793, compound

Product 1

HCID 94206D-Alloisoleucine

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.

Workup

  1. customthe reaction

Sources & evidence

ORD record
ord-8c09f882d44348ec9d94062ff274fe60
Source dataset
uspto-grants-2004_11
Patent number
US06822116B2

Reaction notes

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