N-7-DNA: Synthesis and base pairing of oligonucleotides containing N-7-(2-deoxy-beta-D-erythro-pentofuranosyl)guanine (N(7)G(d))

DC ElementWertSprache
dc.contributor.authorSeela, F
dc.contributor.authorLeonard, P
dc.date.accessioned2021-12-23T16:00:19Z-
dc.date.available2021-12-23T16:00:19Z-
dc.date.issued1996
dc.identifier.issn0018019X
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/4332-
dc.description.abstractThe synthesis of oligonucleotides containing N-7-(2-deoxy-beta-D-erythro-pentofuranosyl)guanine (N(7)G(d); 1) is described. Compound 1 was prepared by nucleobase-anion glycosylation of 2-amino-6-methoxypurine (5) with 2-deoxy-3,5-di-O-(toluoyl)-alpha-D-erythro-pentofuranosyl chloride (6) followed by detoluoylation and displacement of the MeO group (8-->10-->1). Upon base protection with the (dimethylamino)methylidene residue (-->11) the 4,4-dimethoxytrityl group was introduced at OH--C(5')(-->12). The phosphonate 3 and the phosphoramidite 4 were prepared and used in solid-phase oligonucleotide synthesis. The self-complementary dodecamer d(N(7)G-C)(6) shows sigmoidal melting. The T-m of the duplex is 40 degrees. This demonstrates that guanine residues linked via N(7) of purine to the phosphodiester backbone are able to undergo base pairing with cytosine.
dc.language.isoen
dc.publisherNEW SWISS CHEMICAL SOC
dc.relation.ispartofHELVETICA CHIMICA ACTA
dc.subject2'-DEOXYNUCLEOSIDES
dc.subjectBUILDING-BLOCKS
dc.subjectChemistry
dc.subjectChemistry, Multidisciplinary
dc.subjectDNA
dc.subjectHYDROLYSIS
dc.subjectMECHANISM
dc.subjectNUCLEOSIDE ANALOGS
dc.subjectOLIGODEOXYRIBONUCLEOTIDES
dc.subjectSALT GLYCOSYLATION PROCEDURE
dc.subjectSOLID-PHASE SYNTHESIS
dc.subjectSTABILITY
dc.titleN-7-DNA: Synthesis and base pairing of oligonucleotides containing N-7-(2-deoxy-beta-D-erythro-pentofuranosyl)guanine (N(7)G(d))
dc.typejournal article
dc.identifier.doi10.1002/hlca.19960790215
dc.identifier.isiISI:A1996UD12300014
dc.description.volume79
dc.description.issue2
dc.description.startpage477
dc.description.endpage487
dc.publisher.placeVERLAG HELVETICA CHIMICA ACTA, MALZGASSE 21, POSTFACH 313, CH-4010 BASEL, SWITZERLAND
dcterms.isPartOf.abbreviationHelv. Chim. Acta
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