L-Isoleucine → D-Alloisoleucine

HRID 2416154Notes

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 94206D-Alloisoleucine

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.

Workup

customis provided

Sources & evidence

ORD record: ord-0b78521188b54b54a72b7c0dbb8e2ea2
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06822116B2

Reaction notes

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