Process for preparing optically active hydantoins

Details Process for preparing optically active hydantoins Process for preparing optically active hydantoins

1985-09-12

1989-03-14

Kepplinger, Esther M.

Chemistry: molecular biology and microbiology

Process of utilizing an enzyme or micro-organism to destroy...

Resolution of optical isomers or purification of organic...

435121, 435106, C12P 1710, C12P 1304

Patent

active

048124060

ABSTRACT:
A process for preparing optically active hydantoins having the general formula (II): ##STR1## wherein R.sup.1 and R.sup.2, which are different from each other, are independently alkyl group, aralkyl group, aryl group, substituted alkyl group, substituted aralkyl group, or substituted aryl group, or R.sup.1 and R.sup.2 form an asymmetric cyclic compound, characterized in that one configuration of racemic N-carbamoyl-.alpha.-amino acid having the general formula (I): ##STR2## wherein R.sup.1 and R.sup.2 are as above, is enzymatically converted into the corresponding hydantoins.
The present invention provides a process for an optical resolution with a high efficiency which can be used for the synthesis of (S)-6-fluoro-spiro-[chroman-4,4'-imidazolidine]-2',5'-dione (USAN; Sorbinil), which is an optically active hydrantoins attracting public attention as a preventive or a remedy for the particular chronic symptoms of diabetes such as cataract and neuropathy, and (S)-.alpha.-methyl-3,4-dihydroxyphenylalanine (L-methyldopa), which is an optically active amino acid widely used as antihypertensives. Further, the present invention provides a novel finding that N-carbamoyl-.alpha.-amino acid having no hydrogen atom on its .alpha.-carbon atom can be biochemically converted into hydantoins by an enzymatic cyclization reaction.

REFERENCES:
patent: 3964970 (1976-06-01), Dinelli et al.
patent: 4237227 (1980-12-01), Yamada et al.
patent: 4312948 (1982-01-01), Olivieri et al.
patent: 4418146 (1983-11-01), Lungershausen et al.
Lehninger, 1975, Biochemistry, 2nd Ed., Worth Publishers, Inc., pp. 189-191 and 202-205.

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