Unit

UNIT 1.22 O6-(Benzotriazol-1-yl)inosine Derivatives for C6 Modification of Purine Nucleosides

  1. Suyeal Bae1,
  2. Surendra Chaturvedi2,
  3. Mahesh K. Lakshman1

Published Online: 1 MAR 2009

DOI: 10.1002/0471142700.nc0122s36

Current Protocols in Nucleic Acid Chemistry

Current Protocols in Nucleic Acid Chemistry

How to Cite

Bae, S., Chaturvedi, S. and Lakshman, M. K. 2009. O6-(Benzotriazol-1-yl)inosine Derivatives for C6 Modification of Purine Nucleosides. Current Protocols in Nucleic Acid Chemistry. 36:1.22:1.22.1–1.22.23.

Author Information

  1. 1

    The City College and The City University of New York, New York

  2. 2

    PrimeSyn Lab, Hillsborough, New Jersey

Publication History

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

Abstract

A new class of reactive nucleosides, O6-(benzotriazol-1-yl) derivatives of inosine and 2′-deoxyinosine, have been developed via reaction of silyl-protected or unprotected inosine and 2′-deoxyinosine with 1H-benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP). Alternatively, the silyl-protected O6-(benzotriazol-1-yl) derivatives can be synthesized via reaction of protected inosine and 2′-deoxyinosine with triphenylphosphine/iodine/1-hydroxybenzotriazole. These new O6-(benzotriazol-1-yl) inosine derivatives are excellent reagents for the synthesis of other nucleoside analogues via SNAr reaction with a range of nucleophiles. Curr. Protoc. Nucleic Acid Chem. 36:1.22.1-1.22.23. © 2009 by John Wiley & Sons, Inc.

Keywords:

  • inosine;
  • 2′-deoxyinosine;
  • BOP;
  • reactive nucleosides;
  • convertible nucleosides;
  • benzotriazolyl