Unit

UNIT 13.9 Solid-Supported Reagents for Synthesis of Nucleoside Monothiophosphates, Dithiodiphosphates, and Trithiotriphosphates

  1. Yousef Ahmadibeni,
  2. Keykavous Parang

Published Online: 1 MAR 2009

DOI: 10.1002/0471142700.nc1309s36

Current Protocols in Nucleic Acid Chemistry

Current Protocols in Nucleic Acid Chemistry

How to Cite

Ahmadibeni, Y. and Parang, K. 2009. Solid-Supported Reagents for Synthesis of Nucleoside Monothiophosphates, Dithiodiphosphates, and Trithiotriphosphates. Current Protocols in Nucleic Acid Chemistry. 36:13.9:13.9.1–13.9.16.

Author Information

  1. University of Rhode Island, Kingston, Rhode Island

Publication History

  1. Published Online: 1 MAR 2009
  2. Published Print: MAR 2009

Abstract

This unit describes procedures for the selective synthesis of nucleoside monothiophosphates, dithiodiphosphates, and trithiotriphosphates from solid-supported phosphitylating reagents. Rigid and sterically hindered polymer-bound 1,3,2-oxathiaphospholane is reacted selectively with the 5′-hydroxyl group of nucleosides in the presence of 1H-tetrazole. Sulfurization in the presence of Beaucage's reagent (3H-1,2-benzodithiole-3-one 1,1-dioxide) followed by ring-opening with 3-hydroxypropionitrile and basic cleavage in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) through the elimination of polymer-bound ethylene episulfide afford nucleoside monothiophosphates. Furthermore, reaction of polymer-bound diphosphitylating and triphosphitylating reagents, prepared from polymer-bound benzyl alcohol, with unprotected nucleosides, sulfurization with Beaucage's reagent, and acidic cleavage using trifluoroacetic acid cocktail produce nucleoside dithiodiphosphates and trithiotriphosphates in moderate yields. Curr. Protoc. Nucleic Acid Chem. 36:13.9.1-13.9.16. © 2009 by John Wiley & Sons, Inc.

Keywords:

  • solid-phase reagents;
  • nucleosides;
  • monothiophosphorylation;
  • dithiodiphosphorylation;
  • trithiotriphosphorylation;
  • oxathiaphospholane