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3-Deaza-2′-deoxyadenosine: Synthesis via 4-(methylthio)-1H-imidazo[4,5-c]pyridine 2′-deoxyribonucleosides and properties of oligonucleotides

✍ Scribed by Frank Seela; Thomas Grein; Samuel Samnick

Book ID: 102860369
Publisher: John Wiley and Sons
Year: 1992
Tongue: German
Weight: 654 KB
Volume: 75
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19920750519

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✦ Synopsis

Abstract

The synthesis of 4‐(methylthio)‐1__H__‐imidazo[4,5‐c]pyridine 2′‐deoxy‐β‐D‐ribonucleosides 2 and 9 and the conversion of the N^1^‐isomer 2 into the 2′,3′‐didehydro‐2′,3′‐dideoxyribonucleoside 3a or (via 7) 3‐deaza‐2′‐deoxyadenosine (1) is described. Phosphonate building blocks of 1 were employed in solid‐phase synthesis of self‐complementary base‐modified oligonucleotides. Their properties were studied with regard to duplex stability and hydrolysis by the restriction enzyme Eco RI.

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