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]

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

^ ^a ^b 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.
^ 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.
^ ^a ^b 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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[Russ-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.

[PingLi-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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