Unit

UNIT 1.10 Synthesis and Properties of 7-Substituted 7-Deazapurine (Pyrrolo[2,3-d]pyrimidine) 2′-Deoxyribonucleosides

  1. Frank Seela1,2,
  2. Xiaohua Peng1,2

Published Online: 1 JUL 2005

DOI: 10.1002/0471142700.nc0110s21

Current Protocols in Nucleic Acid Chemistry

Current Protocols in Nucleic Acid Chemistry

How to Cite

Seela, F. and Peng, X. 2005. Synthesis and Properties of 7-Substituted 7-Deazapurine (Pyrrolo[2,3-d]pyrimidine) 2′-Deoxyribonucleosides. Current Protocols in Nucleic Acid Chemistry. 21:1.10:1.10.1–1.10.20.

Author Information

  1. 1

    Universität Osnabrück, Osnabrück, Germany

  2. 2

    Center for Nanotechnology (CeNTech), Münster, Germany

Publication History

  1. Published Online: 1 JUL 2005
  2. Published Print: JUN 2005

Abstract

7-Substituted 7-deazapurine (pyrrolo[2,3-d]pyrimidine) 2′-deoxyribonucleosides are synthesized by stereoselective nucleobase anion glycosylation. The introduction of a halogen at C7 is performed regioselectively either on the nucleobase or on the nucleoside. The pKa values of a series of 7-deazapurine 2′-deoxyribonucleosides are provided, and fluorescence properties are also discussed.

Keywords:

  • pyrrolo[2,3-d]pyrimidine;
  • 7-deazapurine;
  • 2′-deoxyribonucleoside;
  • nucleobase anion glycosylation;
  • stereoselectivity;
  • regioselective halogenation;
  • pKa values;
  • fluorescence;
  • quenching