Process for preparing carbamyl derivatives of .alpha.-hydroxy ac

Chemistry: molecular biology and microbiology – Process of utilizing an enzyme or micro-organism to destroy... – Resolution of optical isomers or purification of organic...

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C07B 1902

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active

043329055

ABSTRACT:
This invention relates to a process for preparing carbamyl derivatives of .alpha.-hydroxy acids by the hydrolysis of 5-substituted 2,4-oxazolidinediones.
The carbamyl derivatives can be further hydrolyzed to .alpha.-hydroxy acids.
The invention also relates to a process for the enzymatic hydrolysis of racemic 5-substituted 2,4-oxazolidinediones to give only one of the two possible optical isomers, i.e. the D-carbamyl-.alpha.-hydroxy acid. The free D-.alpha.-hydroxy acid can be obtained from the optically active carbamyl derivative by simple hydrolysis. Of particular interest is the case in which the D-.alpha.-hydroxy acid is D(-)mandelic acid. The enzymatic activity required for preparing the carbamyl derivative of D(-)mandelic acid has been found both in homogenized veal liver and in a series of microorganisms, including Agrobacterium radiobacter, Bacillus brevis, Bacillus stearothermophilus, Pseudomonas sp., Pseudomonas desmolytica, Pseudomonas fluorescens, Pseudomonas putida.

REFERENCES:
patent: 4065353 (1977-12-01), Cecere et al.
patent: 4237227 (1980-12-01), Yamada et al.
patent: 4242452 (1980-12-01), Yamada et al.
Jesse P. Greenstein and Milton Winitz, Chemistry of the Amino Acids, John Wiley & Sons, Inc., vol. 2, pp. 860-863, 1961.
Chemical Abstracts, vol. 91, 170502m, 1979.

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