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Unexpected reversal of the regioselectivity in Thermomyces lanuginosus lipase-catalyzed acylation of floxuridine.

Authors :
Li N
Zong MH
Ma D
Source :
Biotechnology letters [Biotechnol Lett] 2009 Aug; Vol. 31 (8), pp. 1241-4. Date of Electronic Publication: 2009 Apr 11.
Publication Year :
2009

Abstract

Unexpected inversion of the 3':5'-regioselectivity was observed in the enzymatic methacryloylation, crotonylation and cinnamoylation of floxuridine (1.5:1, 2.3:1 and 4.4:1, respectively), where Thermomyces lanuginosus lipase preferentially catalyzed the acylation of 3'-hydroxyl rather than that of 5'-hydroxyl group. The possible reason might be the presence of a remote interaction between the unsaturated bond in the acyl group and the aromatic ring of amino acid residue Trp89 in the lid of the lipase.

Details

Language :
English
ISSN :
1573-6776
Volume :
31
Issue :
8
Database :
MEDLINE
Journal :
Biotechnology letters
Publication Type :
Academic Journal
Accession number :
19360390
Full Text :
https://doi.org/10.1007/s10529-009-0001-x