By H.D. Jakubke, J. Jeschkeit

ISBN-10: 1349025054

ISBN-13: 9781349025053

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There are three different biochemical methods of resolution. ) as a result of the specificity of their oxidases and decarboxylases only metabolise one optical antipode, and leave the other, usually the D-form, unchanged. The second method has only limited preparative application. It uses the enzyme papain, which catalyses the specific formation of amides, in an interesting case of enzymic asymmetric synthesis of amino acids. The most useful enzymic method of optical resolution uses an enzyme to regenerate the free amino acid from a suitable derivative.

The separation can be achieved either by the use of optically active eluants or by interaction with an asymmetric support such as cellulose fibre. RoGOZHIN and DAVANKOV 44 reported the chromatographic resolution of DL-proline using a chlormethylated polystyrene resin incorporating L-proline. Optically pure L-pro)ine was eluted by an ammoniacal solution of copper sulphate: D-proline followed after treatment with aqueous ammonia. Since this work, this procedure has developed into the general technique known as 'ligand chromatography' which can be used successfully to separate the optical antipodes of all the monoamino monocarboxylic acids.

The unprotected amino group of the acid formed is converted into the ammonium salt of the corresponding carbamic acid R-CH(NH-COONH4 )-COOH by the excess of ammonium carbonate, and further reaction to give secondary and tertiary amino compounds is thus suppressed. Higher yields and purer products may be obtained by causing halogenated carboxylic acid esters to react with potassium phthalimide (GABRIEL's method). The phthaloyl group of the N-phthaloyl-amino acid can be removed by acid hydrolysis or reaction with hydrazine.

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