کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
70222 | 48816 | 2012 | 6 صفحه PDF | دانلود رایگان |

A regioselective enzymatic approach to 5′-O-galactosylated derivatives of pyrimidine 2′-deoxynucleosides was described. With o-nitrophenyl β-d-galactoside as glycosyl donor, galactosylation reactions of 2′-deoxynucleosides were mediated by a commercial β-galactosidase from bovine liver, affording 5′-O-galactosylated derivatives with the yields of 45–85% and 5′-regioselectivities of 92–100%. The study of enzyme substrate recognition revealed that the β-galactosidase performance showed a clear dependence on R-group present in the base moiety of 2′-deoxynucleoside. Besides, such desirable products were synthesized with satisfactory yields (41–68%) and moderate to high 5′-regioselectivities (87–100%) by using the crude enzyme extract.
Figure optionsDownload as PowerPoint slideHighlights
► A series of 5′-galactosylated derivatives of pyrimidine 2′-deoxynucleosides were synthesized using bovine liver β-galactosidase with satisfactory yields and good regioselectivities.
► There is a strong correlation between the structures of 2′-deoxynucleosides and the enzyme performance.
► The crude β-glycosidase extract is also a good catalyst for the synthesis of these galactosylated derivatives.
Journal: Journal of Molecular Catalysis B: Enzymatic - Volume 79, July 2012, Pages 35–40