Andrei A. Rodionov

Synthesis and properties of O-beta-D-ribofuranosyl-(1"-2')-adenosine-5"-O-phosphate and its derivatives.

Abstract The synthesis of O-β-D-ribofuranosyl-(1″-2′)-adenosine-5″-O-phosphate and its suitably protected derivative for oligonucleotide synthesis have been developed.

Effective Anomerisation of 2′‐Deoxyadenosine Derivatives During Disaccharide Nucleoside Synthesis

The formation of a disaccharide nucleoside (11) by O3′‐glycosylation of 5′‐O‐protected 2′‐deoxyadenosine or its N 6‐benzoylated derivative has been observed to be accompanied by anomerisation to the corresponding α‐anomeric product (12). The latter reaction can be explained by instability of the N‐glycosidic bond of purine 2′‐deoxynucleosides in the presence of Lewis acids. An independent study on the anomerisation of partly blocked 2′‐deoxyadenosine has been carried out. Additionally, transglycosylation has been utilized in the synthesis of 3′‐O‐β‐d‐ribofuranosyl‐2′‐deoxyadenosines and its α‐anomer.

DISACCHARIDE NUCLEOSIDES AND THEIR ENZYMATIC AND CHEMICAL INCORPORATION INTO OLIGONUCLEOTIDES

Abstract A high yield synthesis of different O-ribofuranosylnucleosides has been achieved. Kinetics of the acid-catalysed hydrolysis of disaccharide nucleosides has been studied. Chemical and enzymatic incorporation of 2′-O-ribofuranosyl-nucleoside residue into oligonucleotides was investigated.

Synthesis of O-β-D-Ribofuranosyl-(1″-2′)-adenosine-5″-O-phosphate

Abstract The first synthesis of O-β-D-ribofuranosyl-(1″-2′)-adenosine-5″-O-phosphate starting from protected 2′-O-β-D-ribofuranosyladenosine has been performed.

Synthesis of 2′‐O‐β‐d‐Ribofuranosylnucleosides

A simple and efficient method for the preparation of 2‐O‐β‐D‐ribofuranosylnucleosides, minor tRNA components, is described in this unit. The method consists of condensation of a small excess of 1‐O‐acetyl‐2,3,5‐tri‐O‐benzoyl‐β‐D‐ribofuranose activated with tin tetrachloride with N‐protected 3,5‐O‐tetra‐isopropyldisiloxane‐1,3‐diyl‐ribonucleosides in 1,2‐dichloroethane. Subsequent deprotection produces 2‐O‐β‐D‐ribofuranosylnucleosides in an overall yield of 46% to 72%.

UNIT 1.14 Synthesis of 2′-O-β-d-Ribofuranosylnucleosides

A simple and efficient method for the preparation of 2‐O‐β‐D‐ribofuranosylnucleosides, minor tRNA components, is described in this unit. The method consists of condensation of a small excess of 1‐O‐acetyl‐2,3,5‐tri‐O‐benzoyl‐β‐D‐ribofuranose activated with tin tetrachloride with N‐protected 3,5‐O‐tetra‐isopropyldisiloxane‐1,3‐diyl‐ribonucleosides in 1,2‐dichloroethane. Subsequent deprotection produces 2‐O‐β‐D‐ribofuranosylnucleosides in an overall yield of 46% to 72%.

Synthesis of 2'-O-beta-d-Ribofuranosylnucleosides.

A simple and efficient method for the preparation of 2‐O‐β‐D‐ribofuranosylnucleosides, minor tRNA components, is described in this unit. The method consists of condensation of a small excess of 1‐O‐acetyl‐2,3,5‐tri‐O‐benzoyl‐β‐D‐ribofuranose activated with tin tetrachloride with N‐protected 3,5‐O‐tetra‐isopropyldisiloxane‐1,3‐diyl‐ribonucleosides in 1,2‐dichloroethane. Subsequent deprotection produces 2‐O‐β‐D‐ribofuranosylnucleosides in an overall yield of 46% to 72%.