Synthesis of (2′S)- and (2′R)-2′-deoxy-2′-[(2- methoxyethoxy)amino] pyrimidine nucleosides and oligonucleotides

Timofei S. Zatsepin, Yulia M. Ivanova, Tatiana S. Oretskaya

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

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 openingof O2,2′-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 Tm 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.

Original languageEnglish
Pages (from-to)1537-1545
Number of pages9
JournalChemistry and Biodiversity
Volume1
Issue number10
DOIs
Publication statusPublished - 2004
Externally publishedYes

Fingerprint

Dive into the research topics of 'Synthesis of (2′S)- and (2′R)-2′-deoxy-2′-[(2- methoxyethoxy)amino] pyrimidine nucleosides and oligonucleotides'. Together they form a unique fingerprint.

Cite this