Racemization of alpha-amino acid esters by aliphatic ketones in the presence of carboxylic acids.
Amino acid esters are racemized by dissolution in a mixture of aliphatic ketones and carboxylic acids. The racemization rate mainly depends on the structure of the amino acid and on the kind of ketone and carboxylic acid used, the best racemizing medium being acetone containing 15% acetic acid. The mechanism of the racemization and the practical consequences of this study in the optical resolution field are discussed.
Barry
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INSERM U 58, Montpellier, France.
Pugnière
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M
Castro
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B
Previero
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A
D000085:Acetates / Q000737:chemistry*; D019342:Acetic Acid; D000096:Acetone / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D004952:Esters / Q000737:chemistry; D009904:Optical Rotation; D013237:Stereoisomerism
D000085:Acetates; D000596:Amino Acids; D004952:Esters; D000096:Acetone; D019342:Acetic Acid