7-substituted 7-deaza-2 `-deoxyadenosines and 8-aza-7-deaza-2 `-deoxyadenosines: Fluorescence of DNA-base analogues induced by the 7-alkynyl side chain

Autor(en): Seela, F
Zulauf, M
Sauer, M
Deimel, M
Stichwörter: 2'-DEOXYRIBOFURANOSIDES; BIOTIN; Chemistry; Chemistry, Multidisciplinary; EMISSION PROPERTIES; HYBRID FORMATION; LABELED OLIGONUCLEOTIDE PROBES; NUCLEIC-ACIDS; NUCLEOSIDES; OLIGODEOXYRIBONUCLEOTIDES; PRIMARY AMINO GROUP; PYRAZOLO<3,4-D>PYRIMIDINES
Erscheinungsdatum: 2000
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: HELVETICA CHIMICA ACTA
Volumen: 83
Ausgabe: 5
Startseite: 910
Seitenende: 927
Zusammenfassung: 
7-Alkynylated 7-deazaadenine (pyrrolo[2.3-d]pyrimidin-4-amine) 2'-deoxyribonucleosides show strong fluorescence which is induced by the 7-alkynyl sids chain ( Table 3). A large Stokes shift with an emission around 400 nm is observed when the compound is irradiated at 280 nm. nle solvent dependence indicates the formation of a charged transition state. The fluorescence appears when the triple bond is in conjugation with the heterocyclic base. Electron-donating substituents at the triple bond increase the fluorescence. Hliile electron-withdrawing residues reduce it. In comparison the 7-alkynylated 8-aza-7-deazaadenine (pyrazolo[3,4-d]pyrimidin-4-amine) 2'-deoxyribunucleosides are rather weakly fluorescent (Table 4). Quantum yields and fluorescence decay rimes are measured. The synthesis of the 7-alkynylated 7-duaLa-'.-dc oxyadenosines and Xa; aza-7-deaza-2'-deoxyadenosines was performed with 7-deaza-2'-deoxy-7- iodoadenosine (6) or 8-aza-7-deaza-2' deoxy-7-iodoadenosine (22) as starting materials and employing the Pd''-catalyzed cross-coupling reaction with the corresponding alkynes (Schemes,1, 4, and 5). Catalytic hydrogenation of the side chain ol. die unsaturated nucleosides 5 and 17 afforded the 7-alkyl derivatives 18 and 19. respectively, which do not show significant fluorescence (Scheme 2).
ISSN: 0018019X
DOI: 10.1002/(SICI)1522-2675(20000510)83:5<910::AID-HLCA910>3.0.CO;2-4

Show full item record

Page view(s)

1
Last Week
0
Last month
1
checked on Feb 23, 2024

Google ScholarTM

Check

Altmetric