Fluorescence properties and base pair stability of oligonucleotides containing 8-aza-7-deaza-2 `-deoxyisoinosine or 2 `-deoxyisoinosine

Autor(en): Seela, F
Becher, G
Chen, YM
Stichwörter: Biochemistry & Molecular Biology; DNA; NUCLEOSIDE; PHOSPHORAMIDITES
Erscheinungsdatum: 2000
Herausgeber: MARCEL DEKKER INC
Journal: NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS
Volumen: 19
Ausgabe: 10-12, SI
Startseite: 1581
Seitenende: 1598
Zusammenfassung: 
The fluorescence and the base pairing properties of 8-aza-7-deaza-2'-deoxyisoinosine (1) are described and compared with those of 2'-deoxyisoinosine (2). The corresponding phosphoramidites (11, 12) are synthesized using the diphenyl-carbamoyl (DPC) residue for the 2-oxo group protection. The nucleosides 1 and 2 base pair with 2'-deoxy-5-methylisocytidine in DNA duplexes with antiparallel chain orientation and with 2'-deoxycytidine in a parallel DNA. These base pairs are less stable than the canonical dA-dT pair and that of 2'-deoxyinosine (4) with 2'-deoxycytidine. The fluorescence of the nucleosides 1 and 2 is quenched (similar to 95%) in duplex DNA. The residual fluorescence is used to determine the T-m-values, which are found to be the same as determined UV-spectrophotometrically.
ISSN: 15257770
DOI: 10.1080/15257770008045448

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