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Issue 4, 2008
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A green, fully enzymatic procedure for amine resolution, using a lipase and a penicillin Gacylase

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Abstract

A green procedure for the kinetic resolution of chiral amines via enzymatic acylation and deacylation has been demonstrated. The fully enzymatic approach obviates the common, waste-generating deacylation under strongly alkaline conditions. The acylating agent was (R)-phenylglycine propyl ester in combination with Candida antarctica lipase B as acylation catalyst. The enantiomerically enriched amides were subsequently deacylated in the presence of the penicillin G acylase from Alcaligenes faecalis. The degree of enantiomer recognition by CaLB in the acylation of aliphatic amines was unexpectedly modest, but a considerable further enantiomeric enrichment could be accomplished in the course of the subsequent enzymatic hydrolysis step.

Graphical abstract: A green, fully enzymatic procedure for amine resolution, using a lipase and a penicillin G acylase

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Publication details

The article was received on 13 Sep 2007, accepted on 18 Dec 2007 and first published on 25 Jan 2008


Article type: Paper
DOI: 10.1039/B714088F
Green Chem., 2008,10, 415-418

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    A green, fully enzymatic procedure for amine resolution, using a lipase and a penicillin G acylase

    H. Ismail, R. M. Lau, L. M. van Langen, F. van Rantwijk, V. K. Švedas and R. A. Sheldon, Green Chem., 2008, 10, 415
    DOI: 10.1039/B714088F

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