Deoxyadenosine - CAS 4754-39-6
Catalog number:
4754-39-6
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C10H13N5O3
Molecular Weight:
251.245
COA:
Inquire
Targets:
Others
Description:
Deoxyadenosine is a substrate of bacterial methylthioadenosine/S-adenosylhomocysteine (MTA/SAH) nucleosidase and a product inhibitor produced by radical SAM enzymes.
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Purity:
≥95%
Appearance:
Solid powder
Synonyms:
5'-deoxyadenosine; 5'-dAdo; (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-methyltetrahydrofuran-3,4-diol;
Solubility:
Soluble in DMSO
Storage:
Store at -20 °C
MSDS:
Inquire
Application:
MTA/SAH nucleosidase
Quality Standard:
Enterprise standard
Shelf Life:
As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly.
Quantity:
Milligrams-Grams
InChIKey:
XGYIMTFOTBMPFP-KQYNXXCUSA-N
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
Canonical SMILES:
C[C@@H]1[C@H]([C@H]([C@@H](O1)n2cnc3c2ncnc3N)O)O
1.Simultaneous determination of 8-oxo-2'-deoxyguanosine and 8-oxo-2'-deoxyadenosine in human retinal DNA by liquid chromatography nanoelectrospray-tandem mass spectrometry.
Ma B1, Jing M1, Villalta PW1, Kapphahn RJ2, Montezuma SR2, Ferrington DA2, Stepanov I1,3. Sci Rep. 2016 Mar 16;6:22375. doi: 10.1038/srep22375.
Age-related macular degeneration (AMD) is the leading cause of blindness among older adults in the developed world. Oxidative damage to mitochondrial DNA (mtDNA) in the retinal pigment epithelium (RPE) may play a key role in AMD. Measurement of oxidative DNA lesions such as 8-oxo-2'-deoxyguanosine (8-oxo-dG) and 8-oxo-2'-deoxyadenosine (8-oxo-dA) in diseased RPE could provide important insights into the mechanism of AMD development. We have developed a liquid chromatography-nanoelectrospray ionization-tandem mass spectrometry method for simultaneous analysis of 8-oxo-dG and 8-oxo-dA in human retinal DNA. The developed method was applied to the analysis of retinal DNA from 5 donors with AMD and 5 control donors without AMD. In mtDNA, the levels of 8-oxo-dG in controls and AMD donors averaged 170 and 188, and 8-oxo-dA averaged 11 and 17 adducts per 10(6) bases, respectively. In nuclear DNA, the levels of 8-oxo-dG in controls and AMD donors averaged 0.
2.Design and synthesis of a novel fluorescent benzo[g]imidazo[4,5-c]quinoline nucleoside for monitoring base-pair-induced protonation with cytosine: distinguishing cytosine via changes in the intensity and wavelength of fluorescence.
Siraiwa S1, Suzuki A1, Katoh R1, Saito Y1. Org Biomol Chem. 2016 Apr 5. [Epub ahead of print]
A novel fluorescent benzo[g]imidazo[4,5-c]quinoline nucleoside () comprising a 3-deaza-2'-deoxyadenosine skeleton was developed and used to monitor -C base-pair formation in oligodeoxynucleotide (ODN) duplexes. The newly synthesized exhibited distinct photophysical properties associated with its protonated/deprotonated forms (monomer: pKa 6.2) via dramatic changes in its absorption and fluorescence spectra. In ODN duplexes, the induced protonation of occurred, even under alkalescent conditions when cytosine was the opposite base on the complementary strand; the resulting -C base pairs were stable. By monitoring the protonation of under neutral and alkalescent conditions, we could clearly discriminate cytosine through spectral changes in absorption and fluorescence. Similarly, we found that the demonstrated 3-deaza-2'-deoxyadenosine forms a stable base pair with cytosine via N1 protonation in ODN duplexes under neutral and acidic conditions (pH < 7.
3.The Equally Important Role of Adenine Derivatives to That of Pyrimidine Derivatives in Near 0 eV Electron-Induced DNA Lesions.
Wang S1, Zhao P2, Zhang C3, Bu Y4. Chemphyschem. 2016 Feb 22. doi: 10.1002/cphc.201600002. [Epub ahead of print]
To explore possible DNA lesions at the A sites in physiological condition, possible bond ruptures in two models, N7-hydrogenated 2'-deoxyadenosine-3'-monophsphate (3'-dA(N7H)MPH) and 2'-deoxyadenosine-5'-monophsphate (5'-dA(N7H)MPH), without and with electron attachment are theoretically studied here. In the neutral case, DNA backbone breaks and base releases resulting respectively from the C3'-O3' and N9-C1' bond ruptures via intramolecular hydrogen transfer are distinctly impossible due to ultrahigh activation energies. After electron attachment, the C3'-O3' and N9-C1' bond ruptures separately in [3'-dA(N7H)MPH]¯ and [5'-dA(N7H)MPH]¯ anions via a pathway of intramolecular PT from the C2' site of 2'-deoxyribose to the C8 of the base moiety are effective.This indicates that substantial DNA backbone breaks and base release can occur at non-3'-end A sites and the 3'-end A site of a single stranded DNA in the physiological environment, respectively.
4.Chemical Constituents of Cordyceps cicadae.
Chu ZB, Chang J, Zhu Y, Sun X. Nat Prod Commun. 2015 Dec;10(12):2145-6.
One new bifuran derivative (1), together with fourteen known compounds, were isolated from Cordyceps cicadae X. Q. Shing. The known compounds included nine nucleosides, uracil (2), uridine (3), 2'-deoxyuridine (4), 2'-deoxyinosine (5), guanosine (6), 2'-deoxyguanosine (7), thymidine (8), adenosine (9), and 2'-deoxyadenosine (10); three amino acids tryptophan (11), phenylalanine (12), and tyrosine (13); and two dopamine analogues N-acetylnoradrenaline (14) and its dimer, trans-2-(3',4'-dihydroxyphenyl)-3-acetylamino-7-(N-acetyl-2"-amino-ethylene)-1,4-benzodioxane (15). Their structures were decisively elucidated by spectroscopic analysis, including 1D and 2D NMR techniques.
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Chemical Structure

CAS 4754-39-6 Deoxyadenosine

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