Enzymatically catalysed decarboxylation of β-carboxyaspartic acid (Asa)

A better synthetic route to β-carboxyaspartic acid (Asa) was achieved through condensation of sodium dibenzyl malonate and benzyl 2-bromoacetate as an alternative to two steps in the method of Koch etal. Catalytic hydrogenation at 5 atm pressure in a shaken stainless steel vessel removed protecting...

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Bibliographic Details
Published in:Canadian journal of chemistry 1990-06, Vol.68 (6), p.886-887
Main Authors: Annett, Robert G, Hassamal, Vanita M, Fishpool, Annette M, Kosakarn, Panadda, Cassamalli, Allen, Allinson, E. Tracey
Format: Article
Language:English
Subjects:
Aliphatic compounds
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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Summary:A better synthetic route to β-carboxyaspartic acid (Asa) was achieved through condensation of sodium dibenzyl malonate and benzyl 2-bromoacetate as an alternative to two steps in the method of Koch etal. Catalytic hydrogenation at 5 atm pressure in a shaken stainless steel vessel removed protecting carbobenzyloxy groups. Asa was purified on a cation exchange column. An extract of E. coli was found to catalyse the decarboxylation of Asa in a doubly coupled assay designed to be specific for produced aspartic acid. Evidence for enzymatic decarboxylation includes complete loss of activity on boiling and progressive loss of activity on repeated freeze-thawing of the extract. Keywords: decarboxylation, β-carboxyaspartic acid, Asa decarboxylase.
ISSN:0008-4042
1480-3291
DOI:10.1139/v90-139