1977
DOI: 10.1021/bi00638a029
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Synthesis and properties of nucleoside 5'-phosphoazidates derived from guanosine and adenosine nucleotides: effect on elongation factors G and Tu dependent reactions

Abstract: A new type of nucleoside poly (5'-phosphate) analogue, nucleoside 5"-phosphoazidate, with an azido group on the terminal phosphate of GTP, ATP, GDP, GMP, AND AMP, has been synthesized by nucleophilic displacement of the corresponding activated nucleosides by azide ion in yields of 25-45%. Guanosine 5-phosphoazidates is readily photolyzed by ultraviolet light; the corresponding adenosine derivative photolyzes more slowly. Guanosine 5'-O-(2-azidodiphosphate) and guanosine 5"-O-(3-azidotrophosphate) are competiti… Show more

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Cited by 12 publications
(8 citation statements)
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“…N 2 under irradiation and covalently attaching to a protein binding site. 20 Interestingly, anion 10 is an isomer of tetrametaphosphate consisting of an azidophosphate substituted trimetaphosphate. The isomer observed in 10 ostensibly results from nucleophile attack at a Q 2 phosphorus rather than attack at a Q 3 phosphorus (Figure 2A).…”
Section: ■ Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…N 2 under irradiation and covalently attaching to a protein binding site. 20 Interestingly, anion 10 is an isomer of tetrametaphosphate consisting of an azidophosphate substituted trimetaphosphate. The isomer observed in 10 ostensibly results from nucleophile attack at a Q 2 phosphorus rather than attack at a Q 3 phosphorus (Figure 2A).…”
Section: ■ Resultsmentioning
confidence: 99%
“…Anion 1 is also a suitable reagent for tetraphosphorylation of inorganic nucleophiles. Treatment with tetrabutylammonium azide ([TBA]­[N 3 ]) cleanly forms compound 10 in 24 h. Relatedly, phosphoazidate analogs of nucleoside 5′-triphosphates have been used as photolabile affinity labels, extruding N 2 under irradiation and covalently attaching to a protein binding site . Interestingly, anion 10 is an isomer of tetrametaphosphate consisting of an azidophosphate substituted trimetaphosphate.…”
Section: Resultsmentioning
confidence: 99%
“…Guanosine triphosphate, 'Reanal', Hungary, was purified by column chromatography on DEAE~ellulose (What- man DE-52) with the use of gradient elution (O.l-0.4 M) triethylammonium bicarbonate buffer (pH 7.5). ~-Azido~anosine tripl~osphate (II) [4] was synthesized at Novosibirsk State University to our order by a method soon to be published. [a-32P]-Uridinetriphosphate with spec.…”
Section: Methodsmentioning
confidence: 99%
“…If the substrate activity of y-derivatives of nucleoside triphosphates is a general property, then by introducing an azide group into various positions, we can modify different sites of the RNA polymerase active centre allowing more thorough investigation of its topography. Here we demonstrate that the y(p)azidobenzylamide of guanosine triphosphate (I) [3] and y-azidoguanosine triphosphate (II) [4] (fig.1) are substrates of RNA polymerase and that they can be used for photoaffinity modification of this enzyme.…”
Section: In~oductionmentioning
confidence: 99%
“…All operations with azido derivatives were carried out in the dark. Other general methods were as described in previous papers (Chládek et al, , 1977. NMR spectra were measured on a JEOL FX-100 in Me2SO-«fe using DSS as the internal standard.…”
Section: General Methodsmentioning
confidence: 99%