Unit

UNIT 2.11 Enzymatic Regioselective Levulinylation of 2′-Deoxyribonucleosides and 2′-O-Methylribonucleosides

  1. Iván Lavandera1,
  2. Javier García1,
  3. Susana Fernández1,
  4. Miguel Ferrero1,
  5. Vicente Gotor1,
  6. Yogesh S. Sanghvi2

Published Online: 1 JUL 2005

DOI: 10.1002/0471142700.nc0211s21

Current Protocols in Nucleic Acid Chemistry

Current Protocols in Nucleic Acid Chemistry

How to Cite

Lavandera, I., García, J., Fernández, S., Ferrero, M., Gotor, V. and Sanghvi, Y. S. 2005. Enzymatic Regioselective Levulinylation of 2′-Deoxyribonucleosides and 2′-O-Methylribonucleosides. Current Protocols in Nucleic Acid Chemistry. 21:2.11:2.11.1–2.11.36.

Author Information

  1. 1

    Universidad de Oviedo, Oviedo, Spain

  2. 2

    Rasayan, Inc., Encinitas, California

Publication History

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

Abstract

The levulinyl-protected nucleosides are key building blocks for the solution-phase synthesis of oligonucleotides. Short and efficient syntheses of 3′- and 5′-O-levulinylated 2′-deoxyribonucleosides and 2′-O-methylribonucleosides have been developed from the corresponding nucleosides by enzyme-catalyzed regioselective acylation in organic solvents or from 3′,5′-di-O-levulinyl derivatives by regioselective enzymatic hydrolysis. Lipase-mediated levulinylation of various nucleosides has been accomplished with acetonoxime levulinate as an acyl donor. Use of immobilized Pseudomonas cepacia lipase (PSL-C) has furnished 3′-O-levulinylated 2′-deoxyribonucleosides in excellent yields. Similarly, Candida antarctica lipase B (CAL-B) has provided 5′-O-levulinylated nucleosides in high yields. 3′-O-Levulinylated 2′-deoxyribonucleosides and 2′-O-methylribonucleosides were prepared via selective hydrolysis of 3′,5′-di-O-levulinate esters using CAL-B.

Keywords:

  • lipases;
  • enzymatic synthesis;
  • enzymatic hydrolysis;
  • enzymatic acylation;
  • levulinylation;
  • 3′-O-levulinyl-2′-deoxyribonucleosides;
  • 3′-O-levulinyl-2′-O-methylribonucleosides;
  • 5′-O-levulinyl-2′-deoxyribonucleosides;
  • 5′-O-levulinyl-2′-O-methylribonucleosides