2'-Deoxyguanosine Chemical Properties

Melting point:

300 °C

Boiling point:

410.43°C (rough estimate)

Density 

1.3382 (rough estimate)

refractive index 

-42 ° (C=0.2, 1mol/L NaOH)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

NH₄OH 1 M: 50 mg/mL, clear to very faintly turbid, yellow to brown

form 

powder

pka

9?+-.0.20(Predicted)

color 

White to Off-white

PH

2.37；9.33

optical activity

Consistent with structure

Water Solubility 

Slightly soluble in water.

λmax

255 (pH 1)

BRN 

39814

InChIKey

OROIAVZITJBGSM-OJFKHTATSA-N

CAS DataBase Reference

961-07-9(CAS DataBase Reference)

NIST Chemistry Reference

Deoxyguanosine(961-07-9)

EPA Substance Registry System

Guanosine, 2'-deoxy- (961-07-9)

Safety Information

Risk Statements 

20/21/22

Safety Statements 

24/25

WGK Germany 

3

RTECS 

MF8760000

F 

10-23

TSCA 

Yes

HS Code 

29349990

MSDS

• Language:English Provider:2'-Deoxyguanosine monohydrate
• Language:English Provider:SigmaAldrich

2'-Deoxyguanosine Usage And Synthesis

Chemical Properties

White crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents.

Uses

2'-Deoxyguanosine (Deoxyguanosine; dG) is composed of the purine nucleoside guanine linked by its N9 nitrogen to the C1 carbon of deoxyribose. It is a purine nucleoside that upon sequential phosphoylation (kinases) forms dGTP which is used by DNA polymerases and reverse transcriptases to synthesis 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.

Definition

ChEBI: 2'-deoxyguanosine 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.

benefits

8-Hydroxy-2'-deoxyguanosine (8-OHdG) is the most commonly used marker of DNA oxidation for the diagnosis of oxidative DNA damage and bipolar disorder (BD), as well as for the prevention of plaque formation and for the inhibition of vascular smooth muscle cell activation through Rac1 inactivation.

Biological Functions

2‘-Deoxyguanosine (2’dGuo) is a purine nucleoside metabolite that has been shown to inhibit proliferation-dependent antigen-specific suppressor T cell (Ts) function in mouse and human systems. 2'dGuo also inhibits mitogen-induced T cell proliferation. Low concentrations (40 gM) of 2'dGuo enhanced phytohemagglutinin- and amantadine A-induced T-cell transformation, possibly due to the inhibition of T-cell function leading to the promotion of T-cell growth factor production. T-cell responses were inhibited only when the concentration of 2'dGuo was toxic to lymphocytes.^[1]

IC 50

Human Endogenous Metabolite

Purification Methods

2'-Deoxyguanosine recrystallises from H2O as the monohydrate. [Brown &C5440 Lythgoe J Chem Soc 1990 1950, L

References

[1] A C HANGLOW; P M L. The effect of 2’deoxyguanosine on human lymphocyte responses. I. 2’deoxyguanosine enhances T lymphocyte responses.[J]. Clinical and experimental immunology, 1985, 59 3: 653-658.

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