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

Autor(en): Seela, F
Leonard, P
Stichwörter: 2'-DEOXYNUCLEOSIDES; BUILDING-BLOCKS; Chemistry; Chemistry, Multidisciplinary; DNA; HYDROLYSIS; MECHANISM; NUCLEOSIDE ANALOGS; OLIGODEOXYRIBONUCLEOTIDES; SALT GLYCOSYLATION PROCEDURE; SOLID-PHASE SYNTHESIS; STABILITY
Erscheinungsdatum: 1996
Herausgeber: NEW SWISS CHEMICAL SOC
Journal: HELVETICA CHIMICA ACTA
Volumen: 79
Ausgabe: 2
Startseite: 477
Seitenende: 487
Zusammenfassung: 
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.
ISSN: 0018019X
DOI: 10.1002/hlca.19960790215

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