Synthesis of DNA/RNA and their analogs via phosphoramidite and H-phosphonate chemistries

Subhadeep Roy; Marvin Caruthers

doi:10.3390/molecules181114268

Synthesis of DNA/RNA and their analogs via phosphoramidite and H-phosphonate chemistries

Molecules. 2013 Nov 18;18(11):14268-84. doi: 10.3390/molecules181114268.

Authors

Subhadeep Roy¹, Marvin Caruthers

Affiliation

¹ Department of Chemistry and Biochemistry, University of Colorado, Boulder, CO 80309, USA. subhadeep.roy@colorado.edu.

Abstract

The chemical synthesis of DNA and RNA is universally carried out using nucleoside phosphoramidites or H-phosphonates as synthons. This review focuses on the phosphorus chemistry behind these synthons and how it has been developed to generate procedures whereby yields per condensation approach 100% with very few side products. Additionally the synthesis and properties of certain DNA and RNA analogs that are modified at phosphorus will also be discussed. These analogs include boranephosphonates, metallophosphonates, and alkylboranephosphines.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Review

MeSH terms

DNA / chemical synthesis*
DNA / chemistry*
Organophosphonates / chemistry*
Organophosphorus Compounds / chemistry*
RNA / chemical synthesis*
RNA / chemistry*

Substances

Organophosphonates
Organophosphorus Compounds
phosphoramidite
RNA
DNA