Chemical and enzymatic synthesis of DNA fragments containing 5-(beta-D-glucopyranosyloxymethyl)-2 '-deoxycytidine - a modified nucleoside in T4 phageDNA

Authors
de Kort, M de Visser, PC Kurzeck, J Meeuwenoord, NJ van der Marel, GA Ruger, W van Boom, JH
Citation
M. De Kort et al., Chemical and enzymatic synthesis of DNA fragments containing 5-(beta-D-glucopyranosyloxymethyl)-2 '-deoxycytidine - a modified nucleoside in T4 phageDNA, EUR J ORG C, (11), 2001, pp. 2075-2082
Citations number
34
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
11
Year of publication
2001
Pages
2075 - 2082
Database
ISI
SICI code
1434-193X(200106):11<2075:CAESOD>2.0.ZU;2-F
Abstract
DNA fragments 23 and 25, containing 5-hydroxymethyl-2'deoxycytidine (5-HMdC ) and 5-(beta -D-glucopyranosyloxymethyl)-2'-deoxycytidine (5-GlcMdC) units , respectively, were assembled by means of a solid support-assisted synthes is using phosphoramidite building blocks 4 and 5, respectively. In addition , 20-mer 23 was converted into fragment 26 by a glycosylation with uridine diphosphoglucose (UDPG), catalyzed by T4 beta -glucosyltransferase (BGT).