Boranophosphate

Boranophosphates are salts with an anion consisting of borane (BH3) and phosphite groups. One of the simplest examples is [(CH3O)2OPBH3]−, prepared by base hydrolysis of the adduct of borane and trimethylphosphite.[2]

Structure of a boranophosphate analogue of ATP, the borane substituent is highlighted in red.[1]

Boranophosphates have gained attention as structural surrogates of phosphate group in living systems. In some compounds, borane replaces of one of the oxygens of a triphosphate or diphosphate functional group. Phosphorus remains tetrahedral, but the BH3-appended phosphorus center is trivalent. Boranophosphates have been incorporated into nucleotides and studied as potential therapeutic and diagnostic agents.[3] They are one of several covalent modifications of phosphodi- and triesters. The compounds are prepared by attaching the borane to the phosphoramidite stage in the synthesis of nucleosides. The P-BH3 bond is sufficiently robust to survive deprotection methods to allow formation of the triphosphate.[3]

Aside from boranophosphates, other modifications of di- and triphosphates include phosphorothioates and methylphosphonate. They also are chiral at phosphorus.[1]

References
  1. Abramova, Tatyana V.; Silnikov, Vladimir N. (2011). "Synthesis and properties of carbohydrate–phosphate backbone-modified oligonucleotide analogues and nucleic acid mimetics". Russian Chemical Reviews. 80 (5): 429–452. Bibcode:2011RuCRv..80..429A. doi:10.1070/RC2011v080n05ABEH004188.
  2. Imamoto, Tsuneo; Nagato, Eiji; Wada, Yoshiyuki; Masuda, Hideki; Yamaguchi, Kentaro; Uchimaru, Tadafumi (1997). "New Boranophosphorylation Reagents, Dimethyl Boranophosphate Monopotassium Salt and Tetramethyl Boranopyrophosphate". Journal of the American Chemical Society. 119 (41): 9925–9926. doi:10.1021/ja972276l.
  3. Li, Ping; Sergueeva, Zinaida A.; Dobrikov, Mikhail; Shaw, Barbara Ramsay (2007). "Nucleoside and Oligonucleoside Boranophosphates: Chemistry and Properties". Chemical Reviews. 107 (11): 4746–4796. doi:10.1021/cr050009p. PMID 17967037.


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