Table of Contents
Metal-Based Drugs
Volume 8, Issue 3, Pages 145-148

New Boron Analogues of Pyrophosphates and Deoxynucleoside Boranophosphates

1Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, IL 60115-2862, USA
2Metallo-Biotech International, Inc., 663 Teal Court, DeKalb, IL 60115-6201, USA

Received 28 May 2001; Accepted 20 June 2001

Copyright © 2001 Hindawi Publishing Corporation. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


Tetraethyldicyanoborane pyrophosphate (2) and 3'-(diethylphosphite-cyanoborano)-5'-dimethoxytrityl.N4-benzoyl-deoxycytidine (3) have been synthesized in 70% and 76% yields, respectively. The compatibility of the substituted boranophosphates with common protecting groups is hereby demonstrated.

Boron containing biologically active compounds, such as nucleosides and nucleotides 1-6 and amino acids 7-9 are important due to their potential therapeutic activity, research and diagnostic applications. Many boron containing compounds have shown promising activity as anticancer, 1,11,12 antiinflammatory,13 and antiosteoporotic 13agents. Oligonucleotdes in which a non-bridging oxygen atom is replaced by a borane(BH3) group are a very important class of modified nucleic acids. 1,3,14-16 The BH3 group is isoelectronic with oxygen in natural oligonucleotides and isoelectronic and isostructural with the oligonucleotide methyl phosphonates, which are nuclease resistant. On the other hand, the α-borano triphosphates are good substrates for DNA polymerases and incorporation of boranophosphates into DNA causes an increase in the resistance to exo- and endonucleases 2,17a as compared to non-modified DNA. There are also notable applications of the α-borano triphosphates in PCR sequencing 17a and nucleic acid detection 17b.