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Synthesis of (2′S)- and (2′R)-2′-Deoxy-2′-[(2-methoxyethoxy)amino] Pyrimidine Nucleosides and Oligonucleotides

✍ Scribed by Timofei S. Zatsepin; Yulia M. Ivanova; Tatiana S. Oretskaya

Publisher
John Wiley and Sons
Year
2004
Tongue
English
Weight
167 KB
Volume
1
Category
Article
ISSN
1612-1872

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✦ Synopsis

Abstract

Syntheses of specified 2′‐modified nucleosides were achieved: a) via oximation of the 5′,3′‐blocked 2′‐oxocytidine, followed by reduction, or b) by intramolecular nucleophilic addition of 3′‐(2‐methoxyethoxy)carbamate to the 2′‐position with opening of O^2^,2′‐anhydrouridine. For the first time, 3′‐phosphoroamidites of these 2′‐modified nucleosides were successfully incorporated into oligonucleotides by solid‐phase synthesis. Incorporation of 2′‐modified nucleotides into oligodeoxyribonucleotides had a negative effect on the duplex T~m~ values with the DNA or RNA complements. Nevertheless, modified nucleotides have shown good target recognition; the (S)‐isomer binds preferably to RNA and the (R)‐isomer to DNA. Both modified nucleosides significantly increased nuclease resistance of the oligodeoxyribonucleotides.

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We describe the stereoselective synthesis of (2'S)-2'-deoxy-2'-C-methyladenosine ( ) and (2'S)-2'-deoxy-2'-C-methylinosine ( ) as well as their corresponding cyanoethyl phosphoramidites 16 and 19 from 6-O-(2,6dichlorophenyl)inosine as starting material. The methyl group at the 2'-position was introd