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 | Enthalten in: | ORGANIC & BIOMOLECULAR CHEMISTRY | Band: | 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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geprüft am 06.06.2024