2000
DOI: 10.1002/1522-2675(20000705)83:7<1392::aid-hlca1392>3.0.co;2-h
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Synthesis of Boron-Containing ADP and GDP Analogues: Nucleoside 5′-(P-Boranodiphosphates)

Abstract: 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 … Show more

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Cited by 20 publications
(16 citation statements)
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“…In recent studies, we have expanded the class of boranophosphates to previously unknown phosphate species. In addition to P ‐borano analogs of cyclic mononucleotides80–82 and diphosphates,83–84 a number of different double‐modified phosphodiesters modified with a borane and either a methyl or a heteroatom were chemically synthesized82,85–89 (Fig. 8).…”
Section: Molecular Family Of Boranophosphatesmentioning
confidence: 99%
“…In recent studies, we have expanded the class of boranophosphates to previously unknown phosphate species. In addition to P ‐borano analogs of cyclic mononucleotides80–82 and diphosphates,83–84 a number of different double‐modified phosphodiesters modified with a borane and either a methyl or a heteroatom were chemically synthesized82,85–89 (Fig. 8).…”
Section: Molecular Family Of Boranophosphatesmentioning
confidence: 99%
“…4 Abstracts Scheme 1 Synthesis of 2-cyanoethyl 2-cyanoethyl N,N,N′,N′-tetraisopropylphosphorodiamidite (C) Lin and colleagues used 2-cyanoethyl N,N,N′,N′-tetraisopropylphosphorodiamidite as the phosphinylating reagent in the presence of diisopropylammonium tetrazolide to couple with 2',3'-di-O-acetyladenosine to generate boron-containing ADP analogues (in an overall yield of 36%). 7 (D) Smith and co-workers developed an efficient method to prepare aldose phosphate diesters using 2-cyanoethyl N,N,N′,N′-tetraisopropylphosphorodiamidite. 8 A 5-O-protected diol was firstly reacted with the phosphinylating reagent and 1H-tetrazole as an activator at room temperature, followed by oxidation, generating cyclic phosphate triester diastereoisomers in high yield.…”
Section: Introductionmentioning
confidence: 99%
“…A similar intramolecular reaction of thymidine 3A-boranophosphorothioate P-diisopropylamidate 8 10 gave compound 5a, but in less than 10% yield. 11 The steric hinderance of a primary and secondary alcohol may account for the reactivity difference between compounds 6 and 8. 12 Since the direct cyclization of boranophosphorothioates was unsuitable, we decided to explore the possibility of introducing the modification into a nucleoside 3A,5A-cyclophosphite.…”
mentioning
confidence: 99%