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

Zsuzsa Veres, András Neszmélyi, Anna Szabolcs, Géza Dénes, Árpád I. Kiss

Research output: Contribution to journalArticle

4 Citations (Scopus)

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 μm for uridine phosphorylase from rat intestinal mucosa. This value is approximately one order of magnitude lower than the Km for uridine (22 μm), 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.

Original languageEnglish
Pages (from-to)1-5
Number of pages5
JournalArchives of Biochemistry and Biophysics
Volume286
Issue number1
DOIs
Publication statusPublished - 1991

Fingerprint

Uridine Phosphorylase
Pyrimidine Nucleosides
Nucleosides
Conformations
Ligands
Uridine
Substrates
Intestinal Mucosa
Rats
Nuclear magnetic resonance
Molecules
Enzymes
indium(III) hydroxide

ASJC Scopus subject areas

  • Biochemistry
  • Biophysics
  • Molecular Biology

Cite this

The effect of the 3′-OH group on the conformation and binding ability of anhydropyrimidine nucleosides to uridine phosphorylase. / Veres, Zsuzsa; Neszmélyi, András; Szabolcs, Anna; Dénes, Géza; Kiss, Árpád I.

In: Archives of Biochemistry and Biophysics, Vol. 286, No. 1, 1991, p. 1-5.

Research output: Contribution to journalArticle

@article{91e291a602e74637b636f320d3497692,
title = "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 μm for uridine phosphorylase from rat intestinal mucosa. This value is approximately one order of magnitude lower than the Km for uridine (22 μm), 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.",
author = "Zsuzsa Veres and Andr{\'a}s Neszm{\'e}lyi and Anna Szabolcs and G{\'e}za D{\'e}nes and Kiss, {{\'A}rp{\'a}d I.}",
year = "1991",
doi = "10.1016/0003-9861(91)90001-Y",
language = "English",
volume = "286",
pages = "1--5",
journal = "Archives of Biochemistry and Biophysics",
issn = "0003-9861",
publisher = "Academic Press Inc.",
number = "1",

}

TY - JOUR

T1 - The effect of the 3′-OH group on the conformation and binding ability of anhydropyrimidine nucleosides to uridine phosphorylase

AU - Veres, Zsuzsa

AU - Neszmélyi, András

AU - Szabolcs, Anna

AU - Dénes, Géza

AU - Kiss, Árpád I.

PY - 1991

Y1 - 1991

N2 - 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 μm for uridine phosphorylase from rat intestinal mucosa. This value is approximately one order of magnitude lower than the Km for uridine (22 μm), 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.

AB - 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 μm for uridine phosphorylase from rat intestinal mucosa. This value is approximately one order of magnitude lower than the Km for uridine (22 μm), 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.

UR - http://www.scopus.com/inward/record.url?scp=0025831862&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0025831862&partnerID=8YFLogxK

U2 - 10.1016/0003-9861(91)90001-Y

DO - 10.1016/0003-9861(91)90001-Y

M3 - Article

C2 - 1897940

AN - SCOPUS:0025831862

VL - 286

SP - 1

EP - 5

JO - Archives of Biochemistry and Biophysics

JF - Archives of Biochemistry and Biophysics

SN - 0003-9861

IS - 1

ER -