Publication
Title
Synthesis of 3'-deoxy-3'-c-hydroxymethyl-aldopentopyranosyl nucleosides and their incorporation in oligonucleotides : part 2, 1
Author
Abstract
The synthesis of 3'-deoxy-3'-C-hydroxymethyl-aldopentopyranosyl nucleosides using an intramolecular radical C-C bond formation reaction is described. This method gives good results for the synthesis of thymine and adenine nucleosides, but not for cytosine and guanine nucleosides. Dependent on the configuration (beta-D-erythro or alpha-L-threo), the conformation of the adenine nucleosides is clearly different (axial base moiety for alpha-D-erythro and equatorial adenine base for alpha-L-threo nucleosides) which could be explained by the gauche effect. Oligonucleotides built up of 2',3'-dideoxy-3'-C-hydroxymethyl-alpha-L-threo-pentopyranosyl adenine are able to form duplexes with oligothymidylate although with less stability than natural dsDNA.
Language
English
Source (journal)
Tetrahedron. - Oxford
Publication
Oxford : 1995
ISSN
0040-4020
Volume/pages
51:45(1995), p. 12319-12336
ISI
A1995TD21800014
Full text (Publisher's DOI)
Full text (publisher's version - intranet only)
UAntwerpen
Faculty/Department
Publication type
Subject
External links
Web of Science
Record
Identification
Creation 11.12.2013
Last edited 16.07.2017