8-azaadenosine and its 2 `-deoxyribonucleoside: Synthesis and oligonucleotide base-pair stability

DC FieldValueLanguage
dc.contributor.authorSeela, F
dc.contributor.authorMunster, I
dc.contributor.authorLochner, U
dc.contributor.authorRosemeyer, H
dc.date.accessioned2021-12-23T15:57:45Z-
dc.date.available2021-12-23T15:57:45Z-
dc.date.issued1998
dc.identifier.issn0018019X
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/3111-
dc.description.abstractThe synthesis of 8-azaadenosine (1a; z(8)A) has been performed by SnCl4-catalyzed glycosylation of 8-azaadenine (4) with 1,2,3,5-tetra-O-acetyl-beta-D-ribofuranose (5), followed by the separation of the regioisomers 6 and 7 and subsequent deacetylation. The ribonucleoside 1a as well as its 2'-deoxy derivative 1b (z(8)A(d)) were converted into oligonucleotide building blocks - the phosphonate 2 as well as the phosphoramidites 3 and 19. They were used to prepare the oligoribonucleotide (z(8)A-U)(6) and oligodeoxyribonucleotides. The T-m values and the thermodynamic data of duplex formation of the modified duplexes showed no significant changes compared to those containing A(d) or A residues. This indicates that the stereoelectronic effect of the 8-azaadenine base which was found for the monomeric nucleoside has only a minor influence on the duplex stability.
dc.language.isoen
dc.publisherWILEY-V C H VERLAG GMBH
dc.relation.ispartofHELVETICA CHIMICA ACTA
dc.subject2',3'-DIDEOXYRIBONUCLEOSIDES
dc.subject2',5'-OLIGOADENYLATES
dc.subject2',5'-OLIGONUCLEOTIDE ANALOGS
dc.subject2'-DEOXYRIBOFURANOSIDES
dc.subject8-AZA-2'-DEOXYGUANOSINE
dc.subjectChemistry
dc.subjectChemistry, Multidisciplinary
dc.subjectDEOXYNUCLEOSIDES
dc.subjectDNA
dc.subjectGLYCOSYLATION
dc.subjectHYBRIDIZATION
dc.subjectNUCLEOSIDES
dc.title8-azaadenosine and its 2 `-deoxyribonucleoside: Synthesis and oligonucleotide base-pair stability
dc.typejournal article
dc.identifier.doi10.1002/hlca.19980810527
dc.identifier.isiISI:000074253200013
dc.description.volume81
dc.description.issue6
dc.description.startpage1139
dc.description.endpage1155
dc.publisher.placeMUHLENSTRASSE 33-34, D-13187 BERLIN, GERMANY
dcterms.isPartOf.abbreviationHelv. Chim. Acta
crisitem.author.deptInstitut für Chemie neuer Materialien-
crisitem.author.deptidinstitute11-
crisitem.author.parentorgFB 05 - Biologie/Chemie-
crisitem.author.grandparentorgUniversität Osnabrück-
crisitem.author.netidRoHe783-
Show simple item record

Page view(s)

1
Last Week
0
Last month
0
checked on Apr 18, 2024

Google ScholarTM

Check

Altmetric