Title
Synthesis of 3'-deoxy-3'-c-hydroxymethyl-aldopentopyranosyl nucleosides and their incorporation in oligonucleotides : part 2, 1 Synthesis of 3'-deoxy-3'-c-hydroxymethyl-aldopentopyranosyl nucleosides and their incorporation in oligonucleotides : part 2, 1
Author
Faculty/Department
Faculty of Pharmaceutical, Biomedical and Veterinary Sciences. Pharmacy
Publication type
article
Publication
Oxford ,
Subject
Chemistry
Source (journal)
Tetrahedron. - Oxford
Volume/pages
51(1995) :45 , p. 12319-12336
ISSN
0040-4020
ISI
A1995TD21800014
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
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.
E-info
https://repository.uantwerpen.be/docman/iruaauth/5494c2/f335935.pdf
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:A1995TD21800014&DestLinkType=RelatedRecords&DestApp=ALL_WOS&UsrCustomerID=ef845e08c439e550330acc77c7d2d848
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:A1995TD21800014&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=ef845e08c439e550330acc77c7d2d848
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:A1995TD21800014&DestLinkType=CitingArticles&DestApp=ALL_WOS&UsrCustomerID=ef845e08c439e550330acc77c7d2d848