5/'-deoxyadenosine


CAS No. : 4754-39-6

5/
Product Details
For research use only. Not Intended for Therapeutic Use!
Cat No:I000087
Synonyms:5/'-deoxyadenosine; 5/'dAdo; 5/'-dAdo.;(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-methyltetrahydrofuran-3,4-diol
Molecular Formula:C10H13N5O3
Molecular Weight:251.246
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Appearance:Solid powder
Purity: > 98%
Cat No:I000087
Cas No:4754-39-6
Product-Name:5/'-deoxyadenosine
IUPAC Name:(2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-methyloxolane-3,4-diol
InChI:InChI=1S/C10H13N5O3/c1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15/h2-4,6-7,10,16-17H,1H3,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
InChIKey:XGYIMTFOTBMPFP-KQYNXXCUSA-N
SMILES:CC1C(C(C(O1)N2C=NC3=C2N=CN=C3N)O)O
5/'-deoxyadenosine, also known as 5/'dAdo or 5/'-dAdo, is a substrate of bacterial methylthioadenosine/S-adenosylhomocysteine (MTA/SAH) nucleosidase and a product inhibitor produced by radical SAM enzymes. 5′-dADO may be useful to study the specificity and distribution of radical S-adenosyl-L-methionine enzymes.

1:Transition State Structure and Inhibition of Rv0091, a 5/'-Deoxyadenosine/5/'-methylthioadenosine Nucleosidase from Mycobacterium tuberculosis. Namanja-Magliano HA, Stratton CF, Schramm VL.ACS Chem Biol. 2016 Jun 17;11(6):1669-76. doi: 10.1021/acschembio.6b00144. Epub 2016 Apr 8. PMID: 27019223
2:Inhibiting NAD+-dependent DNA ligase activity with 2-(cyclopentyloxy)-5/'-deoxyadenosine (CPOdA) offers a new tool for DNA replication and repair studies in the model archaeon Haloferax volcanii. Giroux X, MacNeill SA.FEMS Microbiol Lett. 2015 Nov;362(21). pii: fnv181. doi: 10.1093/femsle/fnv181. Epub 2015 Sep 28. PMID: 26420852
3:5/'-(N-aminoacyl)-sulfonamido-5/'-deoxyadenosine: attempts for a stable alternative for aminoacyl-sulfamoyl adenosines as aaRS inhibitors. Gadakh B, Smaers S, Rozenski J, Froeyen M, Van Aerschot A.Eur J Med Chem. 2015 Mar 26;93:227-36. doi: 10.1016/j.ejmech.2015.02.010. Epub 2015 Feb 9. PMID: 25686591
4:Identification of a 5/'-deoxyadenosine deaminase in Methanocaldococcus jannaschii and its possible role in recycling the radical S-adenosylmethionine enzyme reaction product 5/'-deoxyadenosine. Miller D, O/'Brien K, Xu H, White RH.J Bacteriol. 2014 Mar;196(5):1064-72. doi: 10.1128/JB.01308-13. Epub 2013 Dec 27. PMID: 24375099 Free PMC Article
5:Travels with carbon-centered radicals. 5/'-deoxyadenosine and 5/'-deoxyadenosine-5/'-yl in radical enzymology. Frey PA.Acc Chem Res. 2014 Feb 18;47(2):540-9. doi: 10.1021/ar400194k. Epub 2013 Dec 5. PMID: 24308628
6:Radical SAM activation of the B12-independent glycerol dehydratase results in formation of 5/'-deoxy-5/'-(methylthio)adenosine and not 5/'-deoxyadenosine. Demick JM, Lanzilotta WN.Biochemistry. 2011 Feb 1;50(4):440-2. doi: 10.1021/bi101255e. Epub 2011 Jan 5. PMID: 21182298
7:Antiproliferative and protein kinase binding activities of Some N6, 5/'-bis-ureido 5/'-amino-5/'-deoxyadenosine derivatives. Peterson MA, Oliveira M, Christiansen MA.Nucleosides Nucleotides Nucleic Acids. 2009 May;28(5):394-407. doi: 10.1080/15257770903044432. PMID: 20183591
8:Inhibitors of adenosine consuming parasites through polymer-assisted solution phase synthesis of lipophilic 5/'-amido-5/'-deoxyadenosine derivatives. Heidler P, Zohrabi-Kalantari V, Kaiser M, Brun R, Emmrich T, Link A.Bioorg Med Chem. 2009 Feb 15;17(4):1428-36. doi: 10.1016/j.bmc.2009.01.026. Epub 2009 Jan 20. PMID: 19196516
9:Crystallization and X-ray diffraction of 5/'-fluoro-5/'-deoxyadenosine synthase, a fluorination enzyme from Streptomyces cattleya. Dong C, Deng H, Dorward M, Schaffrath C, O/'Hagan D, Naismith JH.Acta Crystallogr D Biol Crystallogr. 2003 Dec;59(Pt 12):2292-3. Epub 2003 Nov 27. PMID: 14646098
10:Synthesis and evaluation of analogues of 5/'-([(Z)-4-amino-2-butenyl]methylamino)-5/'-deoxyadenosine as inhibitors of tumor cell growth, trypanosomal growth, and HIV-1 infectivity. Marasco CJ Jr, Kramer DL, Miller J, Porter CW, Bacchi CJ, Rattendi D, Kucera L, Iyer N, Bernacki R, Pera P, Sufrin JR.J Med Chem. 2002 Nov 7;45(23):5112-22. PMID: 12408722
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