Process for preparing carbamyl derivatives of .alpha.-hydroxy acids and the corresponding .alpha.-hydroxy acids
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United States of America Patent
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Jun 1, 1982
Grant Date -
N/A
app pub date -
Sep 17, 1980
filing date -
Oct 17, 1979
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Expired
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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.
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