Boranophosphates as Mimics of Natural Phosphodiesters in DNA

Jack   S.   Summers; Barbara   Ramsay   Shaw

doi:10.2174/0929867013372409

Abstract

In boranophosphate-oligodeoxynucleosides (BH 3- -ODN) a borane group replaces one of the two non-bridging oxygen atoms in the phosphodiester backbone of the naturally occurring congener. The chemical and biophysical properties of BH 3 - -ODN are reviewed, as are their interactions with enzymes such as DNA polymerases, exo- and endonucleases, and ribonuclease H. Three approaches to synthesis of BH 3- -ODN are described in solution, on solid supports, and by template directed enzymatic polymerization of appropriately modified nucleoside triphosphates. Comparisons are made to other members of the family of phosphorus modified nucleic acids, the phosphorothioates and methylphosphonates. The potential applications of boranophosphate modified compounds to antisense therapeutics and DNA sequencing are discussed.

Keywords: Boranophosphates, Natural Phosphodiesters, enzymatic polymerization, oligodeoxy nucleoside phosphorothioates, methylphosphonates, phosphoramidates, phosphoro fluoridates, F-ODN, Antisense Agents, Phosphodiester Analogs