Protection of 2'-hydroxy functions of ribonucleosides

Curr Protoc Nucleic Acid Chem. 2001 May:Chapter 2:Unit 2.2. doi: 10.1002/0471142700.nc0202s00.

Abstract

The main purpose of this article is to discuss 2'-protection in the context of effective oligoribonucleotide synthesis. Emphasis is placed on the 2'-protecting groups of choice in the synthesis of oligo-and polyribonucleotides, and the requirements that a protective group must satisfy to become the 2'-hydroxyl-protecting group of choice. Finally, the unit discusses the issue of 2'-O-acyl and 2'-O-silyl group migration to the 3'-hydroxy function of ribonucleosides during protection, along with the consequences of the conditions used for their removal on the stability of internucleotide linkages.

MeSH terms

  • Benzyl Compounds / chemistry
  • Biochemistry / methods*
  • Esters / chemistry
  • Hydrogen-Ion Concentration
  • Hydrolysis
  • Hydroxyl Radical / chemistry*
  • Oligoribonucleotides / chemical synthesis
  • Oligoribonucleotides / chemistry
  • Organophosphorus Compounds / chemistry
  • Organosilicon Compounds / chemistry
  • Piperidines / chemistry
  • Ribonucleosides / chemistry*
  • Uridine / chemistry

Substances

  • Benzyl Compounds
  • Esters
  • Oligoribonucleotides
  • Organophosphorus Compounds
  • Organosilicon Compounds
  • Piperidines
  • Ribonucleosides
  • phosphoramidite
  • t-butyldimethylsilyl compounds
  • Hydroxyl Radical
  • Uridine