Oligonucleotide duplexes containing N-8-glycosylated 8-aza-7-deazaguanine and self-assembly of 8-aza-7-deazapurines on the nucleoside and the oligomeric level

Autor(en): Seela, F
Kroschel, R
Stichwörter: 2'-DEOXYISOGUANOSINE; 8-AZA-7-DEAZAADENINE; BASE-PAIRING PROPERTIES; CHAIN ORIENTATION; Chemistry; Chemistry, Organic; CONSTITUENTS; DNA; NUCLEOBASES; OLIGODEOXYRIBONUCLEOTIDES; PARALLEL; RECOGNITION
Erscheinungsdatum: 2003
Herausgeber: ROYAL SOC CHEMISTRY
Journal: ORGANIC & BIOMOLECULAR CHEMISTRY
Volumen: 1
Ausgabe: 22
Startseite: 3900
Seitenende: 3908
Zusammenfassung: 
The 8-aza-7-deazaguanine N-8-(2'-deoxy-beta-D-ribofuranoside) (1) was synthesized, converted into the phosphoramidite 4 and incorporated into oligonucleotides. Nucleoside 1 forms stable base pairs with 2'-deoxy-5-methylisocytidine in DNA with antiparallel chain orientation (aps) and with 2'-deoxycytidine in duplexes with parallel chains (ps). According to the CD spectra self-complementary oligonucleotides d(1-m(5)isoC)(3) and d(1-C)(3) form autonomous DNA-structures. Neither the nucleoside 1 nor the regularly linked 8-aza-7-deaza-2'-deoxyguanosine form G-like tetrads while the regularly linked 8-aza-7-deaza-2'-deoxyisoguanosine gives higher molecular assemblies which are destroyed by bulky 7-bromo substituents. This was verified on monomeric nucleosides by ESI-MS spectrometry and on oligonucleotides by HPLC analysis.
ISSN: 14770520
DOI: 10.1039/b309485p

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