Collection Symposium Series 2002
DOI: 10.1135/css200205169
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Reading and writing genetic information with boranophosphate (borane phosphate) mimics of nucleotides, DNA, and RNA

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Cited by 7 publications
(11 citation statements)
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“…As seen in the other cases, ,, modification of a phosphoramidate at the phosphorus atom results in a noticeable change of its phosphorus chemical shift: from δ ≈ 7 ppm for a normal phosphoramidate , to δ ≈ 60 ppm for a phosphorothioamidate 20a,b and, as we have found in our studies, to δ ≈ 92 ppm for a boranophosphoramidate . Notably, the residence peak for nucleoside amino acid boranophosphoramidates in 31 P NMR is about the same as that for dinucleoside boranophosphates, which indicates a similar chemical environment for phosphorus in both types of compounds.…”
Section: Resultssupporting
confidence: 81%
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“…As seen in the other cases, ,, modification of a phosphoramidate at the phosphorus atom results in a noticeable change of its phosphorus chemical shift: from δ ≈ 7 ppm for a normal phosphoramidate , to δ ≈ 60 ppm for a phosphorothioamidate 20a,b and, as we have found in our studies, to δ ≈ 92 ppm for a boranophosphoramidate . Notably, the residence peak for nucleoside amino acid boranophosphoramidates in 31 P NMR is about the same as that for dinucleoside boranophosphates, which indicates a similar chemical environment for phosphorus in both types of compounds.…”
Section: Resultssupporting
confidence: 81%
“…The two diastereomers of nucleoside amino acid boranophosphoramidates are expected to have different substrate properties toward phosphoramidases and should be useful for investigating the roles of phosphate and metal ions in biological processes to elucidate the stereochemical and metal requirements of the enzymatic reactions involving phosphoramidases. Moreover, due to the presence of a borane group, the boranophosphoramidates are expected to have increased lipophilicity relative to their parent phosphoramidate compounds, which would facilitate the delivery of prodrugs containing antiviral nucleosides. , All of these advantages in combination with the potential utility as a carrier of 10 B in BNCT make the nucleoside amino acid boranophosphoramidate a useful compound and biochemical tool in antiviral drug research.…”
Section: Discussionmentioning
confidence: 99%
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“…Because a borane group (BH 3 ) is isoelectronic and isosteric with oxygen, yet more hydrophobic, a non-bridging α-P oxygen can be replaced by a BH 3 to give α- P -BH 3 nucleotide analogs [18,19]. The P -boranophosphates are near perfect mimics of natural nucleic acids for reading and writing genetic information with high yield and accuracy [20,21]. The α- P -borano ddNTPs are better chain terminators for drug-resistant viral reverse transcriptases (RTs) than parent ddNTPs [22], and the presence of the α- P -borano group leads to increased stability towards 3′ exonuclease [23] and pyrophosphorolytic repair of a dideoxy nucleoside blocked DNA chain [24], as well as enhanced lipophilicity and other unique properties [25,26,27].…”
Section: Introductionmentioning
confidence: 99%