Synthesis of a tetracyclic 2′-deoxyadenosine analog

A tetracyclic 2′-deoxyadenosine has been synthesized via a Stille biaryl coupling on a protected 6-chloro-7-deaza-7-iodopurine-2′-deoxyribose followed by cyclization. The nucleoside was incorporated into an oligodeoxynucleotide (ODN) and shown to pair with thymine. Graphic

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Bibliographic Details
Published inTetrahedron letters Vol. 40; no. 51; pp. 8969 - 8970
Main Authors Buhr, Chris A., Matteucci, Mark D., Froehler, Brian C.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 17.12.1999
Elsevier
Subjects
7-deaza-2′-deoxyadenosine
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
tetracyclic 2′-deoxyadenosine
tetracyclic 2′-deoxyadenosine
7-deaza-2′-deoxyadenosine
OLIGODEOXYNUCLEOTIDES
tetracyclic 2 '-deoxyadenosine
7-deaza-2 '-deoxyadenosine
STABILITY
OLIGONUCLEOTIDES
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Summary:A tetracyclic 2′-deoxyadenosine has been synthesized via a Stille biaryl coupling on a protected 6-chloro-7-deaza-7-iodopurine-2′-deoxyribose followed by cyclization. The nucleoside was incorporated into an oligodeoxynucleotide (ODN) and shown to pair with thymine. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)01875-4