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Chemical Compound Review:

AC1LABXO (2R,3R,4S,5R)-2-(6-amino-2- azido-purin-9...

Synonyms: KB-20897, CTK1H3560, NSC 36905, FT-0662387, 59587-07-4, ...

King, S.M. et al., Sylvers, L.A. et al., Sugumaran, G. et al., Gunnersen, D. et al., Wower, J. et al., et al.

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Disease relevance of AIDS-184967

Two of the probes were derivatives of E. coli tRNA(Phe) in which adenosines at positions 73 and 76 were replaced by 2-azidoadenosine [1].

High impact information on AIDS-184967

In this report, 8- and 2-azidoadenosine 5'-[gamma-32P]triphosphate were used to examine cerebrospinal fluid (CSF) samples for the presence of an ATP binding protein unique to individuals with Alzheimer disease (AD) [2].
Photoreactive derivatives of yeast tRNA(Phe) containing 2-azidoadenosine (2N3A) at position 73 or 76 have been crosslinked to the peptidyl site of Escherichia coli ribosomes [3].
Photoaffinity labeling of the purified enzyme with 2-azidoadenosine 3',5'-di[5'-32P]phosphate occurred only with the 75-kDa protein, confirming that this is the chondroitin 6-sulfotransferase/keratan sulfotransferase [4].
The photoaffinity analogs 2-azidoadenosine 5'-tri(di)-phosphate (2-N3AT(D)P) and 8-azidoadenosine 5'-triphosphate (8-N3ATP) have been used to probe the substructural organization of the nucleotide binding pockets within the alpha and beta heavy chains of the outer arm dynein from Chlamydomonas flagella [5].
Conformational and allosteric changes in fructose 1,6-bisphosphatase upon photoaffinity labeling with 2-azidoadenosine monophosphate [6].

Biological context of AIDS-184967

Yeast tRNA(Phe), containing the photoreactive nucleoside 2-azidoadenosine at position 37 within the anticodon loop, has been cross-linked to the aminoacyl-tRNA (A) and peptidyl-tRNA (P) binding sites of the Escherichia coli ribosome [7].
Inhibition of adenosine deaminase and of platelet aggregation by 2-azidoadenosine, a photolysable analogue of adenosine [8].

Anatomical context of AIDS-184967

Binding of 2-azidoadenosine [beta-32P]diphosphate to the receptor on intact human blood platelets which inhibits adenylate cyclase [9].

Associations of AIDS-184967 with other chemical compounds

The photoaffinity analog 2-azido-ADP (2-azidoadenosine 5'-diphosphate) was used as a probe of the spinach chloroplast ATP synthase [10].

Gene context of AIDS-184967

Identification of amino acid residues at nucleotide-binding sites of chaperonin GroEL/GroES and cpn10 by photoaffinity labeling with 2-azido-adenosine 5'-triphosphate [11].

References

Topography of the E site on the Escherichia coli ribosome. Wower, J., Scheffer, P., Sylvers, L.A., Wintermeyer, W., Zimmermann, R.A. EMBO J. (1993) [Pubmed]
Detection of glutamine synthetase in the cerebrospinal fluid of Alzheimer diseased patients: a potential diagnostic biochemical marker. Gunnersen, D., Haley, B. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
Labeling the peptidyltransferase center of the Escherichia coli ribosome with photoreactive tRNA(Phe) derivatives containing azidoadenosine at the 3' end of the acceptor arm: a model of the tRNA-ribosome complex. Wower, J., Hixson, S.S., Zimmermann, R.A. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
Purification, photoaffinity labeling, and characterization of a single enzyme for 6-sulfation of both chondroitin sulfate and keratan sulfate. Sugumaran, G., Katsman, M., Drake, R.R. J. Biol. Chem. (1995) [Pubmed]
Structure of the alpha and beta heavy chains of the outer arm dynein from Chlamydomonas flagella. Nucleotide binding sites. King, S.M., Haley, B.E., Witman, G.B. J. Biol. Chem. (1989) [Pubmed]
Conformational and allosteric changes in fructose 1,6-bisphosphatase upon photoaffinity labeling with 2-azidoadenosine monophosphate. Riquelme, P.T., Czarnecki, J.J. J. Biol. Chem. (1983) [Pubmed]
Photochemical cross-linking of the anticodon loop of yeast tRNA(Phe) to 30S-subunit protein S7 at the ribosomal A and P sites. Sylvers, L.A., Kopylov, A.M., Wower, J., Hixson, S.S., Zimmermann, R.A. Biochimie (1992) [Pubmed]
Inhibition of adenosine deaminase and of platelet aggregation by 2-azidoadenosine, a photolysable analogue of adenosine. Cusack, N.J., Born, G.V. Proc. R. Soc. Lond., B, Biol. Sci. (1976) [Pubmed]
Binding of 2-azidoadenosine [beta-32P]diphosphate to the receptor on intact human blood platelets which inhibits adenylate cyclase. Macfarlane, D.E., Mills, D.C., Srivastava, P.C. Biochemistry (1982) [Pubmed]
Localization of the tight ADP-binding site on the membrane-bound chloroplast coupling factor one. Czarnecki, J.J., Abbott, M.S., Selman, B.R. Eur. J. Biochem. (1983) [Pubmed]
Identification of amino acid residues at nucleotide-binding sites of chaperonin GroEL/GroES and cpn10 by photoaffinity labeling with 2-azido-adenosine 5'-triphosphate. Bramhall, E.A., Cross, R.L., Rospert, S., Steede, N.K., Landry, S.J. Eur. J. Biochem. (1997) [Pubmed]

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