Chemical and Enzymatic Synthesis of DNA Fragments Containing 5-(β-D-Glucopyranosyloxymethyl)-2′-deoxycytidine − a Modified Nucleoside in T4 Phage DNA

• Published in: European journal of organic chemistry Vol. 2001; no. 11; pp. 2075 - 2082
• Main Authors: de Kort, Martin, de Visser, Peter C., Kurzeck, Jürgen, Meeuwenoord, Nico J., van der Marel, Gijs A., Rüger, Wolfgang, van Boom, Jacques H.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag GmbH 01.06.2001; WILEY‐VCH Verlag GmbH; Wiley
• Subjects: Bacteriophage T4; Chemistry; Chemistry, Organic; Gluconucleoside; Glucosylation; Oligonucleotides; Physical Sciences; Science & Technology; gluconucleoside; SOLID-PHASE SYNTHESIS; D-GLUCOSYL-HYDROXYMETHYLURACIL; oligonucleotides; CLEAVAGE; NUCLEIC-ACIDS; NUCLEOTIDES; BETA-GLUCOSYLTRANSFERASE; MODIFIED BASE J; BACTERIOPHAGE-T4; glucosylation; EXPRESSION; BINDING; bacteriophage T4
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/1099-0690(200106)2001:11<2075::AID-EJOC2075>3.0.CO;2-J

DNA fragments 23 and 25, containing 5‐hydroxymethyl‐2′‐deoxycytidine (5‐HMdC) and 5‐(β‐D‐glucopyranosyloxymethyl)‐2′‐deoxycytidine (5‐GlcMdC) units, respectively, were assembled by means of a solid support‐assisted synthesis 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 β‐glucosyltransferase (BGT).