Oligonucleotides containing pyrazolo[3,4-d]pyrimidines: The influence of 7-substituted 8-aza-7-deaza-2 `-deoxyguanosines on the duplex structure and stability

Autor(en): Seela, F
Becher, G
Stichwörter: 7-DEAZA-2'-DEOXYGUANOSINE; ACID; ANALOGS; CHAINS; Chemistry; Chemistry, Multidisciplinary; DNA; OLIGODEOXYNUCLEOTIDES; PYRAZOLO<3,4-D>PYRIMIDINE
Erscheinungsdatum: 1999
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: HELVETICA CHIMICA ACTA
Volumen: 82
Ausgabe: 10
Startseite: 1640
Seitenende: 1655
Zusammenfassung: 
Oligonucleotides containing 7-substituted 8-aza-7-deazaguanines (= 6-amino-1,5-dihydro-4H-pyrazolo[3.4-d]pyrimidin-4-ones) were prepared by automated solid-phase synthesis. A series of 7-alkynylated 8-aza-7-deaza-2'-deoxyguanosines (see 4a-d)were synthesized with the 7-iodonucleoside 3c as starting material and by the Pd-0/Cu-I-catalyzed cross-coupling reaction with various alkynes. Phosphoramidites were prepared from the 7-substituted 8-aza-7-deaza-2'-deoxyguanosine derivatives carrying halogeno, cyano, and hexynyl substituents. From the melting profiles of oligonucleotide duplexes. the T-m values as well as the thermodynamic data were determined. A significant duplex stabilization by the 7-substituents was observed for the DNA . DNA duplexes, but not in the case of DNA . RNA hybrids.
ISSN: 0018019X
DOI: 10.1002/(SICI)1522-2675(19991006)82:10<1640::AID-HLCA1640>3.0.CO;2-N

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