5'-deoxyadenosine
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MedKoo CAT#: 407245

CAS#: 4754-39-6

Description: 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.


Chemical Structure

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5'-deoxyadenosine
CAS# 4754-39-6

Theoretical Analysis

MedKoo Cat#: 407245
Name: 5'-deoxyadenosine
CAS#: 4754-39-6
Chemical Formula: C10H13N5O3
Exact Mass: 251.1018
Molecular Weight: 251.246
Elemental Analysis: C, 47.81; H, 5.22; N, 27.88; O, 19.10

Price and Availability

Size Price Availability Quantity
1.0g USD 4950.0 2 Weeks
2.0g USD 7950.0 2 Weeks
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Synonym: 5'-deoxyadenosine; 5'dAdo; 5'-dAdo.

IUPAC/Chemical Name: (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-methyltetrahydrofuran-3,4-diol

InChi Key: XGYIMTFOTBMPFP-KQYNXXCUSA-N

InChi Code: 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

SMILES Code: O[C@H]1[C@H](N2C=NC3=C(N)N=CN=C23)O[C@H](C)[C@H]1O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 251.246 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Giroux X, MacNeill SA. 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. FEMS Microbiol Lett. 2015 Nov;362(21). pii: fnv181. doi: 10.1093/femsle/fnv181. Epub 2015 Sep 28. PubMed PMID: 26420852.

2: Gadakh B, Smaers S, Rozenski J, Froeyen M, Van Aerschot A. 5'-(N-aminoacyl)-sulfonamido-5'-deoxyadenosine: attempts for a stable alternative for aminoacyl-sulfamoyl adenosines as aaRS inhibitors. Eur J Med Chem. 2015 Mar 26;93:227-36. doi: 10.1016/j.ejmech.2015.02.010. Epub 2015 Feb 9. PubMed PMID: 25686591.

3: Miller D, O'Brien K, Xu H, White RH. Identification of a 5'-deoxyadenosine deaminase in Methanocaldococcus jannaschii and its possible role in recycling the radical S-adenosylmethionine enzyme reaction product 5'-deoxyadenosine. J Bacteriol. 2014 Mar;196(5):1064-72. doi: 10.1128/JB.01308-13. Epub 2013 Dec 27. PubMed PMID: 24375099; PubMed Central PMCID: PMC3957708.

4: Frey PA. Travels with carbon-centered radicals. 5'-deoxyadenosine and 5'-deoxyadenosine-5'-yl in radical enzymology. Acc Chem Res. 2014 Feb 18;47(2):540-9. doi: 10.1021/ar400194k. Epub 2013 Dec 5. PubMed PMID: 24308628.

5: Demick JM, Lanzilotta WN. Radical SAM activation of the B12-independent glycerol dehydratase results in formation of 5'-deoxy-5'-(methylthio)adenosine and not 5'-deoxyadenosine. Biochemistry. 2011 Feb 1;50(4):440-2. doi: 10.1021/bi101255e. Epub 2011 Jan 5. PubMed PMID: 21182298.

6: Peterson MA, Oliveira M, Christiansen MA. Antiproliferative and protein kinase binding activities of Some N6, 5'-bis-ureido 5'-amino-5'-deoxyadenosine derivatives. Nucleosides Nucleotides Nucleic Acids. 2009 May;28(5):394-407. doi: 10.1080/15257770903044432. PubMed PMID: 20183591.

7: Heidler P, Zohrabi-Kalantari V, Kaiser M, Brun R, Emmrich T, Link A. Inhibitors of adenosine consuming parasites through polymer-assisted solution phase synthesis of lipophilic 5'-amido-5'-deoxyadenosine derivatives. Bioorg Med Chem. 2009 Feb 15;17(4):1428-36. doi: 10.1016/j.bmc.2009.01.026. Epub 2009 Jan 20. PubMed PMID: 19196516.

8: Dong C, Deng H, Dorward M, Schaffrath C, O'Hagan D, Naismith JH. Crystallization and X-ray diffraction of 5'-fluoro-5'-deoxyadenosine synthase, a fluorination enzyme from Streptomyces cattleya. Acta Crystallogr D Biol Crystallogr. 2003 Dec;59(Pt 12):2292-3. Epub 2003 Nov 27. PubMed PMID: 14646098.

9: Marasco CJ Jr, Kramer DL, Miller J, Porter CW, Bacchi CJ, Rattendi D, Kucera L, Iyer N, Bernacki R, Pera P, Sufrin JR. 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. J Med Chem. 2002 Nov 7;45(23):5112-22. PubMed PMID: 12408722.

10: Warncke K, Utada AS. Interaction of the substrate radical and the 5'-deoxyadenosine-5'-methyl group in vitamin B(12) coenzyme-dependent ethanolamine deaminase. J Am Chem Soc. 2001 Sep 5;123(35):8564-72. PubMed PMID: 11525664.

11: LoBrutto R, Bandarian V, Magnusson OT, Chen X, Schramm VL, Reed GH. 5'-Deoxyadenosine contacts the substrate radical intermediate in the active site of ethanolamine ammonia-lyase: 2H and 13C electron nuclear double resonance studies. Biochemistry. 2001 Jan 9;40(1):9-14. PubMed PMID: 11141051.

12: Bandarian V, Poyner RR, Reed GH. Hydrogen atom exchange between 5'-deoxyadenosine and hydroxyethylhydrazine during the single turnover inactivation of ethanolamine ammonia-lyase. Biochemistry. 1999 Sep 21;38(38):12403-7. PubMed PMID: 10493808.

13: Ding KH, Liang NC. Inhibition of 5'-chloro-5'-deoxyadenosine on phosphoinositide and protein phosphorylation in swine platelets. Zhongguo Yao Li Xue Bao. 1995 May;16(3):247-50. PubMed PMID: 7660821.

14: Zhao X, Kao JL, Taylor JS. Preparation and characterization of a deoxyoligonucleotide 49-mer containing a site-specific thymidylyl-(3',5')-deoxyadenosine photoproduct. Biochemistry. 1995 Jan 31;34(4):1386-92. PubMed PMID: 7827086.

15: Byers TL, Wechter RS, Hu RH, Pegg AE. Effects of the S-adenosylmethionine decarboxylase inhibitor, 5'-([(Z)-4-amino-2-butenyl]methylamino)-5'-deoxyadenosine, on cell growth and polyamine metabolism and transport in Chinese hamster ovary cell cultures. Biochem J. 1994 Oct 1;303 ( Pt 1):89-96. PubMed PMID: 7945270; PubMed Central PMCID: PMC1137561.

16: Yakubu MA, Majumder S, Kierszenbaum F. Inhibition of S-adenosyl-L-methionine (AdoMet) decarboxylase by the decarboxylated AdoMet analog 5'-([(Z)-4-amino-2-butenyl]methylamino)-5'-deoxyadenosine (MDL 73811) decreases the capacities of Trypanosoma cruzi to infect and multiply within a mammalian host cell. J Parasitol. 1993 Aug;79(4):525-32. PubMed PMID: 8331473.

17: Stjernborg L, Heby O, Mamont P, Persson L. Polyamine-mediated regulation of S-adenosylmethionine decarboxylase expression in mammalian cells. Studies using 5'-([(Z)-4-amino-2-butenyl]methylamino)-5'-deoxyadenosine, a suicide inhibitor of the enzyme. Eur J Biochem. 1993 Jun 15;214(3):671-6. PubMed PMID: 8319678.

18: Zhang C, Bowlin T, Mirkin BL. Suppression of C-1300 murine neuroblastoma cell proliferation in tissue culture and tumor growth in vivo by (Z)5'-fluoro-4',5'-didehydro-5'-deoxyadenosine (MDL 28,842), an irreversible inhibitor of S-adenosyl-L-homocysteine hydrolase. Oncol Res. 1993;5(10-11):433-9. PubMed PMID: 8054704.

19: Byers TL, Ganem B, Pegg AE. Cytostasis induced in L1210 murine leukaemia cells by the S-adenosyl-L-methionine decarboxylase inhibitor 5'-([(Z)-4-amino-2-butenyl]methylamino)-5'-deoxyadenosine may be due to hypusine depletion. Biochem J. 1992 Nov 1;287 ( Pt 3):717-24. PubMed PMID: 1445235; PubMed Central PMCID: PMC1133067.

20: Shantz LM, Stanley BA, Secrist JA 3rd, Pegg AE. Purification of human S-adenosylmethionine decarboxylase expressed in Escherichia coli and use of this protein to investigate the mechanism of inhibition by the irreversible inhibitors, 5'-deoxy-5'-[(3-hydrazinopropyl)methylamino]adenosine and 5'-([(Z)-4-amino-2-butenyl]methylamino)-5'-deoxyadenosine. Biochemistry. 1992 Jul 28;31(29):6848-55. PubMed PMID: 1637820.