Method of producing enantiomerically pure, open-chain N-alkyl-L

Details Method of producing enantiomerically pure, open-chain N-alkyl-L Method of producing enantiomerically pure, open-chain N-alkyl-L

1992-05-20

1994-09-20

Robinson, Douglas W.

Chemistry: molecular biology and microbiology

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

Resolution of optical isomers or purification of organic...

435228, 435874, C12P 4100, C12N 980

Patent

active

053488822

ABSTRACT:
A method of producing enantiomerically pure, open-chain N-alkyl-L or D amino acids which can be carried out with good yields and without excessive or expensive purification and suitable for industrial production. A racemic mixture of an open-chain N-acyl-N-alkyl amino acid is split by means of a stereospecific amino acylase coordinated with an enantiomerically pure N-acyl-N-alkyl-L or D amino acid to yield one of the antipodes to the corresponding, enantiomerically pure, open-chain N-alkyl-L or D amino acid. Then, either the remaining initial compound or the cleavage product is separated. The enantiomerically pure, open-chain N-alkyl amino acids are useful, for e.g. cyclosporins.

REFERENCES:
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patent: 5120652 (1992-06-01), Groeger et al.
patent: 5219741 (1993-06-01), Groeger et al.
Groeger U. et al., Angew Chem. Int Ed Engl 31:195-7 (1992).
Igloi K. et al., Proc. Hung. Annu. Meet. Biochem. 15:107-8 (1975) (abstract).
Jones, J., Tetrahedron 42:3351-3403 (1986).
Journal of the American Chemical Society 80:3349-55 (1958).

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