Unit

UNIT 1.8 Synthesis, Characterization, and Application of Substituted Pyrazolopyrimidine Nucleosides

  1. Robert O. Dempcy,
  2. Mikhail A. Podyminogin,
  3. Michael W. Reed

Published Online: 1 FEB 2003

DOI: 10.1002/0471142700.nc0108s11

Current Protocols in Nucleic Acid Chemistry

Current Protocols in Nucleic Acid Chemistry

How to Cite

Dempcy, R. O., Podyminogin, M. A. and Reed, M. W. 2003. Synthesis, Characterization, and Application of Substituted Pyrazolopyrimidine Nucleosides. Current Protocols in Nucleic Acid Chemistry. 11:1.8:1.8.1–1.8.15.

Author Information

  1. Epoch Biosciences, Bothell, Washington

Publication History

  1. Published Online: 1 FEB 2003
  2. Published Print: DEC 2002

Abstract

This unit describes, in detail, the preparation of 3-aminopropyl-substituted pyrazolo[3,4-d]pyrimidine analogs of the purines deoxyadenosine (dA) and deoxyguanosine (dG). Phosphoramidite reagents of these so-called aminopropyl-PPA and -PPG nucleosides (AP-PPA and AP-PPG, respectively) allow introduction of amino linkers into internal positions of synthetic DNA strands. Synthesis of suitably protected AP-PPA and AP-PPG phosphoramidites are described. The stepwise alkynylation, hydrogenation, selective protection, and phosphoramidite synthesis is similar for both the PPA and PPG analogs. To demonstrate the application of these reagents, a protocol is given in which a simple DNA strand is synthesized and conjugated to a lipophilic activated ester (dabcyl-SE) to form a stable amide linkage. Utility of this chemistry for preparing internally modified DNA conjugates is discussed.