Catalytic antibodies enantioselectively hydrolysing amino acid e

Details Catalytic antibodies enantioselectively hydrolysing amino acid e Catalytic antibodies enantioselectively hydrolysing amino acid e

1996-11-15

1999-03-23

Patterson, Jr., Charles L.

Chemistry: molecular biology and microbiology

Enzyme , proenzyme; compositions thereof; process for...

Catalytic antibody

435280, 435346, C12N 900, C12N 512, C12S 1300

Patent

active

058858164

DESCRIPTION:

BRIEF SUMMARY
BACKGROUND OF THE INVENTION

1. Field of the Invention
The present invention belongs to the field of the art synthesizing optically active amino acids. Specifically, the present invention relates to a process for conducting enantioselective hydrolysis by utilizing catalytic antibodies. More specifically, the invention relates to processes for enantioselectively hydrolyzing amino acid ester derivatives with catalytic antibodies to effect optical resolution of racemic mixture of amino acid derivatives and to prepare optically active amino acids. Because the present invention allows very easy production of optically active amino acids having various substituted groups, it can contribute to basic studies on the function of living bodies, development of a novel medical drug containing optically active amino acids as an essential component, and development of methodologies for synthesizing various optically and physiologically active substances or functional compounds, which methodologies use optically active amino acids in synthesizing processes.
2. Description of the Related Art
Proteins, a primary component of the living body, are constructed with optically active amino acids, which makes a chiral environment in the living body. Therefore, many of the physiologically active substances including medical drugs are optically active substances, and it is known that bioactivity is found only in either one of enantiomers, or difference in bioactivity is observed between the enantiomers. Accordingly, developing a methodology for obtaining optically active substances is one of the targets of investigations.
The simplest process usually performed to obtain an optically active amino acid derivatives is optical resolution of racemic mixture of amino acid derivatives. The process for optical resolution includes a process employing an enzyme (e.g. a kinetic optical resolution using aminoacylase, lipase and the like) and a process forming a diastereomer, or the like. However, most suitable process must be selected depending on a particular amino acid to be resolved, because there is no common process effective for all the amino acids having a variety of substituted groups.
In such a situation as mentioned above, the inventors of the present invention have succeeded in developing a process for performing optical resolution of racemic mixture of amino acid derivatives, using catalytic antibodies, which is applicable for any amino acids. Although reactions using catalytic antibodies usually have drawbacks in that the catalytic antibodies have substrate specificity, and therefore, they have only limited applicablity, the present inventors have overcome such drawbacks by developing catalytic antibodies which enantioselectively hydrolyze ester derivatives of racemic mixture of any amino acid derivatives to produce corresponding optically active amino acids.


SUMMARY OF THE INVENTION

The present invention relates to a process for performing optical resolution of recemic body of amino acids, characterized by using catalytic antibodies enantioselectively hydrolyzing amino acid ester derivatives.
In another aspect, the present invention relates to a process for preparing optically active amino acids from racemic mixture of amino acid derivatives, characterized by using catalytic antibodies to enantioselectively hydrolyze amino acid ester derivatives.
The processes of the invention can be applied to the synthesis of both L- and D-isomers of amino acids and include two processes each consisting of the following two steps: derivatives, and then derivatives; and derivatives, and then derivatives.
The catalytic antibodies as used herein are typically prepared by immunizing a mammal with, as a hapten, a compound having of the formula 3 below: ##STR2## wherein CBZ is benzyloxycarbonyl.
Although CBZ in formula 3 is an amino-protecting group, other conventional amino-protecting groups known to those skilled in the art, for example, trichloroacetyl, benzyl, t-butoxycarbonyl, 9-fluorenylmethoxycarbonyl, or CBZ having a substituent such as lo

REFERENCES:
patent: 5190865 (1993-03-01), Schultz
patent: 5250426 (1993-10-01), Lerner et al.
Tanaka, F., et al. (1996) J. Amer. Chem Soc. 118, 2332-2339.
Pollack, S. J., et al., (1989) J. Am. Chem. Soc. 111, 5961-5962.
Guo, J., et. al. (1994) J. Am. Chem. Soc. 116, 6062-6069.

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