SYNTHESIS, BASE PAIRING, AND STRUCTURAL TRANSITIONS OF OLIGODEOXYRIBONUCLEOTIDES CONTAINING 8-AZA-2'-DEOXYGUANOSINE

Autor(en): SEELA, F
LAMPE, S
Stichwörter: 7-DEAZA-2'-DEOXYGUANOSINE; BUILDING-BLOCKS; Chemistry; Chemistry, Multidisciplinary; CONFORMATION; DG; DOUBLE HELICAL DNA; SEQUENCE; SOLID-PHASE SYNTHESIS; TELOMERIC DNA; TETRAPLEX FORMATION; THERMODYNAMICS
Erscheinungsdatum: 1994
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: HELVETICA CHIMICA ACTA
Volumen: 77
Ausgabe: 4
Startseite: 1003
Seitenende: 1017
Zusammenfassung: 
The synthesis of oligonucleotides containing 8-aza-2'-deoxyguanosine (z(8)G(d); 1) or its N-8-regioisomer z(8)G(d)(*) (2) instead of 2'-deoxyguanosine (G(d)) is described. For this purpose, the NH2 group of 1 and 2 was protected with a (dimethylamino)methylidene residue (-->5, 6), a 4,4'-dimethoxytrityl group was introduced at 5'-OH (--> 7, 8), and the phosphonates 3a and 4 as well as the phosphoramidite 3b were prepared. These building blocks were used in solid-phase oligonucleotide synthesis. The oligonucleotides were characterized by enzymatic hydrolysis and melting curves (T-m values). The thermodynamic data of the oligomers 12-15 indicate that duplexes were stabilized when 1 was replacing G(d). The aggregation of d(T-G-G-G-G-T) (18) was studied by RP18 HPLC, gel electrophoresis and CD spectroscopy and compared with that of oligonucleotides containing an increasing number of z(8)G(d) residues instead of Gd Similarly to [d(C-G)](3) (12a), the hexamer d(C-z(8)G-C-z(8)G-C-G) (14) underwent salt-dependent B-Z transition.
ISSN: 0018019X
DOI: 10.1002/hlca.19940770413

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