Synthesis of Poly(ADP-ribose) Monomer Containing 2'-O-α-D-Ribofuranosyl Adenosine

Sergey N Mikhailov; Mikhail S Drenichev; Vladimir E Oslovsky; Irina V Kulikova; Piet Herdewijn

doi:10.1002/cpnc.92

Synthesis of Poly(ADP-ribose) Monomer Containing 2'-O-α-D-Ribofuranosyl Adenosine

Curr Protoc Nucleic Acid Chem. 2019 Sep;78(1):e92. doi: 10.1002/cpnc.92.

Authors

Sergey N Mikhailov¹, Mikhail S Drenichev¹, Vladimir E Oslovsky¹, Irina V Kulikova¹, Piet Herdewijn²

Affiliations

¹ Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Moscow, Russia.
² Rega Institute, Katholieke Universiteit Leuven, Leuven, Belgium.

PMID: 31529780
DOI: 10.1002/cpnc.92

Abstract

In this article, the earlier reported procedure for the synthesis of 2'-O-β-D-ribofuranosyl nucleosides was extended to the synthesis of 2'-O-α-D-ribofuranosyl adenosine, a monomeric unit of poly(ADP-ribose). It consists in condensation of a small excess of 1-O-acetyl-2,3,5-tri-O-benzoyl-α,β-D-arabinofuranose activated with tin tetrachloride with 3',5'-O-tetra-isopropyldisiloxane-1,3-diyl-ribonucleosides in 1,2-dichloroethane. The following debenzoylation and silylation of arabinofuranosyl residue and inversion of configuration at C-2'' atom of arabinofuranosyl residue and final removal of silyl protective groups gave 2'-O-α-D-ribofuranosyl adenosine in overall 13% to 21% yield. © 2019 by John Wiley & Sons, Inc.

Keywords: disaccharide nucleosides; monomeric unit; poly(ADP-ribose); synthesis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Adenosine / chemistry*
Poly Adenosine Diphosphate Ribose / chemical synthesis*

Substances

Poly Adenosine Diphosphate Ribose
Adenosine