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

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.

journal_name

Biotechnol Lett

journal_title

Biotechnology letters

authors

Li N,Zong MH,Ma D

doi

10.1007/s10529-009-0001-x

subject

Has Abstract

pub_date

2009-08-01 00:00:00

pages

1241-4

issue

8

eissn

0141-5492

issn

1573-6776

journal_volume

31

pub_type

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