7-DEAZAGUANOSINE - SYNTHESIS OF AN OLIGORIBONUCLEOTIDE BUILDING-BLOCK AND DISAGGREGATION OF THE U-G-G-G-G-U G4 STRUCTURE BY THE MODIFIED BASE

DC FieldValueLanguage
dc.contributor.authorSEELA, F
dc.contributor.authorMERSMANN, K
dc.date.accessioned2021-12-23T15:57:47Z-
dc.date.available2021-12-23T15:57:47Z-
dc.date.issued1993
dc.identifier.issn0018019X
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/3133-
dc.description.abstractBuilding blocks derived from 7-deazaguanosine (c7G, 1) were prepared for solid-phase oligoribonucleotide synthesis. Compound 1 was converted into the isobutyryl derivative 2b and the (dimethylamino)methylidene compound 3 (Scheme 1). After tritylation (--> 4a, b), silylation was studied with regard to regioselectivity. It was found that the triisopropylsilyl group in combination with the (dimethylamino)methylidene residue gave the highest 2'-selectivity (--> 5e). The 2'-O-silyl derivative 5e was reacted with PCl3 affording the 3'-phosphonate 7 which was used in solid-phase oligoribonucleotide synthesis. Oligonucleotides derived from U-G-G-G-G-U with an increasing number of c7G residues instead of G were synthesized. Aggregation was studied by polyacrylamide-gel electrophoresis and CD spectroscopy. Disaggregation of the G4-Structure of U-G-G-G-G-U was observed when c7G replaced G, demonstrating that guanine N(7) participates in the aggregation process.
dc.language.isoen
dc.publisherNEW SWISS CHEMICAL SOC
dc.relation.ispartofHELVETICA CHIMICA ACTA
dc.subjectCHEMICAL SYNTHESIS
dc.subjectChemistry
dc.subjectChemistry, Multidisciplinary
dc.subjectH-PHOSPHONATES
dc.subjectNUCLEOSIDE
dc.subjectRNA
dc.subjectSOLID-PHASE SYNTHESIS
dc.subjectTELOMERIC DNA
dc.title7-DEAZAGUANOSINE - SYNTHESIS OF AN OLIGORIBONUCLEOTIDE BUILDING-BLOCK AND DISAGGREGATION OF THE U-G-G-G-G-U G4 STRUCTURE BY THE MODIFIED BASE
dc.typejournal article
dc.identifier.doi10.1002/hlca.19930760404
dc.identifier.isiISI:A1993LK93400003
dc.description.volume76
dc.description.issue4
dc.description.startpage1435
dc.description.endpage1449
dc.publisher.placeVERLAG HELVETICA CHIMICA ACTA, MALZGASSE 21, POSTFACH 313, CH-4010 BASEL, SWITZERLAND
dcterms.isPartOf.abbreviationHelv. Chim. Acta
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