| Identification | Back Directory | [Name]
2'-DEOXYGUANOSINE | [CAS]
312693-72-4 | [Synonyms]
DG
DEOXYGUANOSINE-2'
2'-DEOXYGUANOSINE
A-2'-DEOXYGUANOSINE
5′-Nucleotides &
2'-DEOXY-D-GUANOSINE
Adenosine Impurity 16
GUANINE DESOXYRIBOSIDE
2'-DEOXYGUANOSINE USP/EP/BP
[3'-2H]2'-deoxyguanosine Monohydrate
2'-Deoxyguanosine-[15N5] monohydrate
9-(2'-DEOXY-BETA-D-RIBOFURANOSYL)GUANINE
[2',2''-2H2]2'-deoxyguanosine Monohydrate
2'-Deoxyguanosine Monohydrate(2'-dG ? H?O)
[1',2',3',4',5'-13C5]2'-deoxyguanosine Monohydrate
Adenosine Impurity 16（2’ Deoxyguanosine Monohydrate） | [EINECS(EC#)]
628-392-4 | [Molecular Formula]
C10H13N5O4 | [MDL Number]
MFCD00080300 | [MOL File]
312693-72-4.mol | [Molecular Weight]
267.24 |
| Chemical Properties | Back Directory | [Melting point ]
>300 °C (dec.)(lit.)
| [storage temp. ]
Refrigerator | [solubility ]
NH4OH 1 M: 50 mg/mL, clear to very faintly turbid, yellow to brown
| [form ]
powder
| [pka]
pK1:2.5(+1) (25°C,μ=0.1) | [color ]
White to Off-White | [biological source]
synthetic (organic) | [BRN ]
39814 | [InChI]
InChI=1/C10H13N5O4/c11-10-13-8-7(9(18)14-10)12-3-15(8)6-1-4(17)5(2-16)19-6/h3-6,16-17H,1-2H2,(H3,11,13,14,18)/t4-,5+,6+/s3 | [InChIKey]
LZSCQUCOIRGCEJ-FPKZOZHISA-N | [SMILES]
OC[C@H]1O[C@@H](N2C3=C(C(NC(=N3)N)=O)N=C2)C[C@@H]1O |&1:2,4,17,r| |
| Hazard Information | Back Directory | [Description]
2''-Deoxyguanosine is a purine nucleoside with diverse biological activities.1,2,3,4 It inhibits the clonogenic growth of HL-60 and K562 leukemia cells (IC50s = 80 and 100 μM, respectively).1 2''-Deoxyguanosine inhibits the growth of MOLT-4 T cells and MGL-8 B cells by 99.8 and 68.3%, respectively, when used at a concentration of 50 μM.2 It increases the number of binucleated cells, a marker of inhibited cytokinesis, in A. sativum meristems.3 2''-Deoxyguanosine (>1 μM) also induces relaxation of precontracted isolated bovine lingual artery.4 | [Chemical Properties]
White to Off-White Solid | [Uses]
Nucleoside analog. | [Application]
2′-Deoxyguanosine monohydrate has been used as a nucleoside supplement:
to study its effect on mitochondrial DNA copy number in deoxyguanosine kinase (dguok) mutant zebrafish,
in tissue culture medium for deoxyribonucleotide triphosphate (dNTP) synthesis,
in RPMI (Roswell Park Memorial Institute)-1640 medium to eliminate the endogenous thymocytes. | [Definition]
ChEBI: 2'-Deoxyguanosine monohydrate is a purine 2'-deoxyribonucleoside having guanine as the nucleobase. It has a role as a Saccharomyces cerevisiae metabolite, a human metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a purines 2'-deoxy-D-ribonucleoside and a purine 2'-deoxyribonucleoside. It is functionally related to a guanosine. | [Biological Functions]
lu et al. found that 2'-Deoxyguanosine (2-dG) is a key immune signaling molecule in plant–microbe interactions and that Arabidopsis VENOSA4 (VEN4) is essential for plant immunity. 2-dG is the immunoreactive component in ZhiNengCong (ZNC). This compound induced classical immune responses, including ROS production, allose accumulation and MPKs phosphorylation, and upregulated the expression of plant immunity-associated genes. In addition, 2-dG-induced plant immunity requires salicylic acid (SA) receptor NPR1 (but not SA), ethylene (ET) signaling, pattern-recognition receptors/coreceptors (PRRs/coreceptors) and the ATP receptor P2K1[1]. VEN4 was involved in 2-dG biosynthesis and could convert dGTP to 2-dG. | [Biochem/physiol Actions]
Deoxyguanosine (dG) is a purine nucleoside that upon sequential phosphorylation (kinases) forms deoxyguanosine triphosphate (dGTP) which is used by DNA polymerases and reverse transcriptases to synthesize DNA(s). Deoxyguanosine is the most electron-rich of the four canonical bases and includes many nucleophilic sites which are susceptible to oxidative damage. This makes deoxyguanosine and its oxidized derivatives useful reagents to study mechanisms of oxidative damage to nucleosides and nucleotides. | [Synthesis]
In 250ml triangular flasks filled with 50ml medium, which contains beef paste 1%, peptone 1%, yeast paste 0.5%, NaCl 0.5%, pH 7.0, sterilized at 118 ℃ for 30min, cooled to access the Pseudomonas aeruginosa QD96, incubated at 30 ℃ oscillation (200r/min) | [storage]
Store at -20°C | [References]
[1] Chongchong Lu . “Discovery of a novel nucleoside immune signaling molecule 2′-deoxyguanosine in microbes and plants.” Journal of Advanced Research 46 (2023): Pages 1-15. |
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