N-7-DNA: Synthesis and base pairing of oligonucleotides containing N-7-(2-deoxy-beta-D-erythro-pentofuranosyl)guanine (N(7)G(d))
DC Element | Wert | Sprache |
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dc.contributor.author | Seela, F | |
dc.contributor.author | Leonard, P | |
dc.date.accessioned | 2021-12-23T16:00:19Z | - |
dc.date.available | 2021-12-23T16:00:19Z | - |
dc.date.issued | 1996 | |
dc.identifier.issn | 0018019X | |
dc.identifier.uri | https://osnascholar.ub.uni-osnabrueck.de/handle/unios/4332 | - |
dc.description.abstract | The 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.iso | en | |
dc.publisher | NEW SWISS CHEMICAL SOC | |
dc.relation.ispartof | HELVETICA CHIMICA ACTA | |
dc.subject | 2'-DEOXYNUCLEOSIDES | |
dc.subject | BUILDING-BLOCKS | |
dc.subject | Chemistry | |
dc.subject | Chemistry, Multidisciplinary | |
dc.subject | DNA | |
dc.subject | HYDROLYSIS | |
dc.subject | MECHANISM | |
dc.subject | NUCLEOSIDE ANALOGS | |
dc.subject | OLIGODEOXYRIBONUCLEOTIDES | |
dc.subject | SALT GLYCOSYLATION PROCEDURE | |
dc.subject | SOLID-PHASE SYNTHESIS | |
dc.subject | STABILITY | |
dc.title | N-7-DNA: Synthesis and base pairing of oligonucleotides containing N-7-(2-deoxy-beta-D-erythro-pentofuranosyl)guanine (N(7)G(d)) | |
dc.type | journal article | |
dc.identifier.doi | 10.1002/hlca.19960790215 | |
dc.identifier.isi | ISI:A1996UD12300014 | |
dc.description.volume | 79 | |
dc.description.issue | 2 | |
dc.description.startpage | 477 | |
dc.description.endpage | 487 | |
dc.publisher.place | VERLAG HELVETICA CHIMICA ACTA, MALZGASSE 21, POSTFACH 313, CH-4010 BASEL, SWITZERLAND | |
dcterms.isPartOf.abbreviation | Helv. Chim. Acta |
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geprüft am 13.05.2024