Process for preparing carbamyl derivatives of .alpha.-hydroxy acids and the corresponding .alpha.-hydroxy acids

US4332905A · kind A · utility

Assignee

• E.N.I. Ente Nozionale Idrocarburi · IT

Inventors

• Roberto Olivieri · Siena, IT
• Giancarlo Eletti Bianchi · Roma, IT
• Eugenio Fascetti · Roma, IT
• Felice Centini · Roma, IT
• Ludwig Degen · Roma, IT
• Walter Marconi · San Donato Milanese, IT

Key dates

• Filing date: Sep 17, 1980
• Grant date: Jun 1, 1982
• Expiry date: Sep 17, 2000

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C12P13/02
• WIPO field: Biotechnology
• WIPO sector: Chemistry

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.