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