The effect of the 3'-OH group on the conformation and binding ability of anhydropyrimidine nucleosides to uridine phosphorylase.

Abstract:

:2,2'-Anhydro-3'-deoxy-5-ethyluridine, a new pyrimidine nucleoside analog, has been examined in terms of its binding potency to uridine phosphorylase, and its conformation in solution (NMR) was studied. 2,2'-Anhydro-3'-deoxy-5-ethyluridine has a Ki value of 3.4 microM for uridine phosphorylase from rat intestinal mucosa. This value is approximately one order of magnitude lower than the Km for uridine (22 microM), the natural substrate. The presence of the 3'-OH group (in the ribo-configuration) on pyrimidine nucleoside analogs may not be considered a prerequisite for the binding to uridine phosphorylase; however, it enhances the binding in the case of flexible ligands cooperating in the process of conformation change toward a more favorable enzyme-ligand interaction. The presence of the 3'-OH group in pyrimidine nucleosides seems to be essential if the molecule is to become a substrate.

journal_name

Arch Biochem Biophys

authors

Veres Z,Neszmélyi A,Szabolcs A,Kiss AI,Dénes G

doi

10.1016/0003-9861(91)90001-y

subject

Has Abstract

pub_date

1991-04-01 00:00:00

pages

1-5

issue

1

eissn

0003-9861

issn

1096-0384

pii

0003-9861(91)90001-Y

journal_volume

286

pub_type

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