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.


Price and Availability

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1g
USD 4950
Size
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2g
USD 7950
Size
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5g
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5'-deoxyadenosine is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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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


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


Technical Data

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).

Harmonized System Code:
293490


References

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.