Chelation-controlled regioselective alkylation of pyrimidine 2'-deoxynucleosides

R Lucas; K Teste; R Zerrouki; Y Champavier; M Guilloton

doi:10.1016/j.carres.2009.10.021

Chelation-controlled regioselective alkylation of pyrimidine 2'-deoxynucleosides

Carbohydr Res. 2010 Jan 26;345(2):199-207. doi: 10.1016/j.carres.2009.10.021. Epub 2009 Oct 30.

Authors

R Lucas¹, K Teste, R Zerrouki, Y Champavier, M Guilloton

Affiliation

¹ Laboratoire de Chimie des Substances Naturelles EA1069, Faculté des Sciences et Techniques, 123 Avenue, Albert Thomas, F-87060 Limoges, France.

PMID: 19932891
DOI: 10.1016/j.carres.2009.10.021

Abstract

Protection-deprotection steps, which are usually needed for regioselective alkylation of pyrimidine deoxynucleosides, can be avoided by choosing the appropriate solvent. The combined effects of low dielectric constant and possible sodium chelation by pyrimidine nucleosides may account for the unexpected regioselectivity observed in THF.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkylation
Chelating Agents / chemistry*
Crown Ethers / chemistry
Deoxycytidine / chemistry
Deoxyuridine / chemistry
Electric Impedance
Pyrimidine Nucleosides / chemistry*
Solvents / chemistry
Stereoisomerism
Substrate Specificity
Thymidine / chemistry

Substances

Chelating Agents
Crown Ethers
Pyrimidine Nucleosides
Solvents
Deoxycytidine
Thymidine
Deoxyuridine