2'-Deoxyguanosine monohydrate Chemical Properties

Melting point:

>300 °C (dec.)(lit.)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

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|

Safety Information

Hazard Codes 

Xn,T

Risk Statements 

22-25

Safety Statements 

45

WGK Germany 

3

F 

10-23

TSCA 

Yes

HS Code 

2934999090

Storage Class

11 - Combustible Solids

MSDS

• Language:English Provider:SigmaAldrich

2'-Deoxyguanosine monohydrate Usage And Synthesis

Description

2''-Deoxyguanosine is a purine nucleoside with diverse biological activities. It inhibits the clonogenic growth of HL-60 and K562 leukemia cells (IC₅₀s = 80 and 100 μM, respectively). 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. It increases the number of binucleated cells, a marker of inhibited cytokinesis, in A. sativum meristems. 2''-Deoxyguanosine (>1 μM) also induces relaxation of precontracted isolated bovine lingual artery.

Chemical Properties

White to Off-White Solid. Soluble in NH4OH 1 M: 50 mg/mL, clear to very faintly turbid.

Uses

2′-Deoxyguanosine monohydrate has been used in stromal cell purification. It has also been used for the quantification of whole cell dNTP (deoxyribonucleotide triphosphate).

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.

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.

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) culture for 16h, will be the culture solution by 4000r/min freezing centrifugation The culture solution was frozen and centrifuged at 4000r/min for 30min, then washed with 0.05mol/L phosphate buffer (pH7.0) and centrifuged again, and the resultant organisms were kept refrigerated as nucleotide phosphorylase for spare parts.

In a 100 ml round bottom flask, loaded with 50 ml of substrate solution containing guanosine and thymidine concentration of 40 mol/L, phosphate buffer for 25 mmol/L, the amount of bacterial body added to 5% (wet weight), stirring reaction at 60 in a constant temperature water bath for 2h, the reaction was completed, frozen centrifugation to remove the bacterial body and a small amount of thymine precipitates. Then the solution was detected by HPLC which contained 24 mmol/L deoxyguanosine with a conversion rate of 60%. After separation by anion exchange resin, 0.26 g of deoxyguanosine was obtained.

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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