Oligonucleoside Boranophosphate (Borane Phosphonate)

Shaw, Barbara Ramsay; Madison, Jon; Sood, Anup; Spielvogel, Bernard F.

doi:10.1385/0-89603-281-7:225

Cited by 20 publications

(46 citation statements)

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“…The borane group is isoelectronic with the oxygen atom but the distribution of charge density is different and boranophosphate analogues are generally less hydrophilic, less sensitive to nuclease when compared to normal nucleic acids, and demonstrate improved substrate properties. As a consequence, boranophosphates and their analogues were shown as promising alternatives in antiviral therapy when nucleoside reverse transcriptase inhibitors were involved [20,21]. In this context, Alvarez et al synthesized a boranophosphinate 18, analogue of AZT (Scheme 2) [22].…”

Section: Reverse Transcriptase Inhibitors Of Hivmentioning

confidence: 99%

Synthesis and Biological Applications of Phosphinates and Derivatives

Virieux

Volle

Bakalara

et al. 2014

Topics in Current Chemistry

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This review first outlines general considerations on phosphinic acids and derivatives as bioisosteric groups. The next sections present key aspects of phosphinic acid-based molecules and include a brief description of the biological pathways involved for their activities. The synthetic aspects and the biological activities of such compounds reported in the literature between 2008 and 2013 are also described.

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Section: Reverse Transcriptase Inhibitors Of Hivmentioning

confidence: 99%

Synthesis and Biological Applications of Phosphinates and Derivatives

Virieux

Volle

Bakalara

et al. 2014

Topics in Current Chemistry

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“…For example, the nucleoside triphosphate analogues, nucleoside 5'-P a -boranotriphosphates (dNTPaB and NTPaB), are good substrates for DNA and RNA polymerases [7] [9]. Yet, after incorporation, the boranophosphate linkages in DNA or RNA are more resistant to endo-and exonucleases than normal phosphodiesters [6] [10]. Here, we investigated methods to synthesize new diphosphate analogues of ADP and GDP.…”

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confidence: 99%

Synthesis of Boron-Containing ADP and GDP Analogues: Nucleoside 5′-(P-Boranodiphosphates)

Lin

Shaw

2000

HCA

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New 5'-(P a -boronated) analogues of the naturally occurring nucleoside diphosphates ADP and GDP were synthesized in good yields, i.e., adenosine 5'-(P a -boranodiphosphate) (ADPaB; 5a) and guanosine 5'-(P aboranodiphosphate) (GDPaB; 5b). Their diastereoisomers were successfully separated by reversed-phase HPLC, and chemical structures were established via spectroscopic methods. The isoelectronic substitution of borane (BH 3 ) for one of the non-bridging O-atoms in phosphate diesters should impart an increase in lipophilicity and change in polarity in ADPaB and GDPaB. The boronated nucleoside diphosphates could be employed for investigations of the stereochemical course and metal requirements of enzymatic reactions involving ADP and GDP, and as carriers of 10 B in boron neutron-capture therapy (BNCT) for the treatment of cancer.

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“…[6,34,35] Despite the extensive study of boranophosphate nucleoside analogues, the exploration of the parent inorganic boranophosphate has not been reported. The various potential applications of a phosphate isoster, together with the limitations of the currently available isosters, justify the continued search for the perfect inorganic phosphate mimic.…”

Section: Discussionmentioning

confidence: 99%

Boranophosphate Salts as an Excellent Mimic of Phosphate Salts: Preparation, Characterization, and Properties

Nahum

Fischer

2004

Eur J Inorg Chem

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We report on the preparation of boranophosphate salts, BPi (2), and the exploration of their properties with a view to developing a new mimic of the parent phosphate. BPi salts were easily prepared in excellent yield in a one-pot two-step reaction from tris(trimethylsilyl) phosphite, and were characterized by X-ray crystallography and IR, 1 H and 31 P NMR spectroscopy. We evaluated the acid/base character of BPi by determining its acidity constants. Likewise, we evaluated the stability of BPi at various pH values, and calculated the decomposition-rate constants at highly acidic pH. We also monitored the H-bonded clustering of BPi in organic solvents, including MeOH. Finally, we explored the chemical behavior of BPi with respect to various organic and inorganic reagents.

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Oligonucleoside Boranophosphate (Borane Phosphonate)

Cited by 20 publications

References 0 publications

Synthesis and Biological Applications of Phosphinates and Derivatives

Synthesis and Biological Applications of Phosphinates and Derivatives

Synthesis of Boron-Containing ADP and GDP Analogues: Nucleoside 5′-(P-Boranodiphosphates)

Boranophosphate Salts as an Excellent Mimic of Phosphate Salts: Preparation, Characterization, and Properties

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