DC Element | Wert | Sprache |
dc.contributor.author | Ramzaeva, Natalya | |
dc.contributor.author | Michalek, Elisabeth | |
dc.contributor.author | Kazimierczuk, Zygmunt | |
dc.contributor.author | Seela, Frank | |
dc.contributor.author | Rosemeyer, Helmut | |
dc.date.accessioned | 2021-12-23T16:13:38Z | - |
dc.date.available | 2021-12-23T16:13:38Z | - |
dc.date.issued | 2007 | |
dc.identifier.issn | 16121872 | |
dc.identifier.uri | https://osnascholar.ub.uni-osnabrueck.de/handle/unios/10665 | - |
dc.description.abstract | Various 2-substituted 2'-deoxyadenosines and 7-deazaadenosines have been synthesized. The phosphonate building block 9 of 2-chloro-7-deaza-2'-deoxyadenosine (7-deazacladribine; 2) was prepared by 4,4'-dimethoxytritylation of the parent nucleoside (-> 7), followed by protection of the amino function with a formamidine residue (-> 8). The latter was reacted with PCl3/N-methylmorpholine/1,2,4-triazole to give compound 9. Moreover, 2-methoxy-2'-deoxyadenosine (2'-deoxyspongosine; 1b) was converted into the fully protected derivative 12, which was then transformed into the 2-cyanoethyl phosphoramidite 14. Also the 2-(trifluoromethyl)-substituted 2'-deoxyadenosines 19-21 were prepared by glycosylation of the chromophore 16 with the halogenose 17, followed by one-pot deprotection and nucleophilic displacement of the 6-Cl substituent. The new DNA building blocks 9 and 14 were used - together with formerly prepared cladribine derivative 4 - for solid-phase synthesis of a series of oligodeoxyribonucleotides. These were studied with respect to their thermal stability as well as of the base pairing mode (Watson-Crick vs. Hoogsteen) of modified bases. | |
dc.language.iso | en | |
dc.publisher | WILEY-V C H VERLAG GMBH | |
dc.relation.ispartof | CHEMISTRY & BIODIVERSITY | |
dc.subject | 2-CHLORO-2'-DEOXYADENOSINE 5'-TRIPHOSPHATE | |
dc.subject | B-DNA DODECAMER | |
dc.subject | Biochemistry & Molecular Biology | |
dc.subject | Chemistry | |
dc.subject | Chemistry, Multidisciplinary | |
dc.subject | DEOXYADENOSINE ANALOGS | |
dc.subject | DEOXYCYTIDINE KINASE | |
dc.subject | DUPLEX STABILIZATION | |
dc.subject | MOLECULAR-STRUCTURE | |
dc.subject | PHOTOCHEMICAL CONVERSION | |
dc.subject | PROTECTING GROUPS | |
dc.subject | SODIUM-SALT GLYCOSYLATION | |
dc.subject | TRIPLE-HELIX | |
dc.title | Hoogsteen vs. Watson-Crick base pairing: Incorporation of 2-substituted adenine- and 7-deazaadenine 2 `-deoxy-beta-d-ribonucleosides into oligonucleotides | |
dc.type | journal article | |
dc.identifier.doi | 10.1002/cbdv.200790222 | |
dc.identifier.isi | ISI:000252235500004 | |
dc.description.volume | 4 | |
dc.description.issue | 12 | |
dc.description.startpage | 2725 | |
dc.description.endpage | 2744 | |
dc.publisher.place | PO BOX 10 11 61, D-69451 WEINHEIM, GERMANY | |
dcterms.isPartOf.abbreviation | Chem. Biodivers. | |
crisitem.author.dept | Institut für Chemie neuer Materialien | - |
crisitem.author.deptid | institute11 | - |
crisitem.author.parentorg | FB 05 - Biologie/Chemie | - |
crisitem.author.grandparentorg | Universität Osnabrück | - |
crisitem.author.netid | RoHe783 | - |