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961-07-9

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961-07-9 Usage

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.

Purification Methods

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

Check Digit Verification of cas no

The CAS Registry Mumber 961-07-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,6 and 1 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 961-07:
(5*9)+(4*6)+(3*1)+(2*0)+(1*7)=79
79 % 10 = 9
So 961-07-9 is a valid CAS Registry Number.

961-07-9 Well-known Company Product Price

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  • TCI America

  • (D0052)  2'-Deoxyguanosine Hydrate  >98.0%(T)

  • 961-07-9

  • 1g

  • 390.00CNY

  • Detail
  • TCI America

  • (D0052)  2'-Deoxyguanosine Hydrate  >98.0%(T)

  • 961-07-9

  • 5g

  • 990.00CNY

  • Detail
  • TCI America

  • (D0052)  2'-Deoxyguanosine Hydrate  >98.0%(T)

  • 961-07-9

  • 25g

  • 3,850.00CNY

  • Detail
  • Alfa Aesar

  • (L14519)  2'-Deoxyguanosine hydrate, 99%   

  • 961-07-9

  • 100mg

  • 267.0CNY

  • Detail
  • Alfa Aesar

  • (L14519)  2'-Deoxyguanosine hydrate, 99%   

  • 961-07-9

  • 500mg

  • 1066.0CNY

  • Detail

961-07-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 2'-deoxyguanosine

1.2 Other means of identification

Product number -
Other names DEOXYGUANOSINE-2'

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:961-07-9 SDS

961-07-9Synthetic route

diphenylmethylsulfonium tetrafluoroborate
10504-60-6

diphenylmethylsulfonium tetrafluoroborate

9-(2'-deoxyribofuranosyl)guanine
961-07-9

9-(2'-deoxyribofuranosyl)guanine

A

O6-methyl 2'-deoxyguanosine
76567-63-0

O6-methyl 2'-deoxyguanosine

B

1-methyl-2'-deoxyguanosine
5132-79-6

1-methyl-2'-deoxyguanosine

Conditions
ConditionsYield
With potassium hydroxide In water; N,N-dimethyl-formamide at 20℃; for 5h;A 4%
B 95%
tris(trimethyl)silyltriflate

tris(trimethyl)silyltriflate

9-(2'-deoxyribofuranosyl)guanine
961-07-9

9-(2'-deoxyribofuranosyl)guanine

2-Amino-(2-deoxy-β-D-erythropentofuranosyl)adenine

2-Amino-(2-deoxy-β-D-erythropentofuranosyl)adenine

Conditions
ConditionsYield
With chloro-trimethyl-silane; ammonia; 1,1,1,3,3,3-hexamethyl-disilazane In methanol; water; toluene24.2%
4-(carbethoxynitrosamino)-1-(3-pyridyl)-1-butanone
68743-68-0

4-(carbethoxynitrosamino)-1-(3-pyridyl)-1-butanone

9-(2'-deoxyribofuranosyl)guanine
961-07-9

9-(2'-deoxyribofuranosyl)guanine

A

4-(3-pyridyl)-4-oxobutanol
59578-62-0

4-(3-pyridyl)-4-oxobutanol

B

(E)-4-(pyridin-3-yl)but-3-en-2-one
100021-45-2

(E)-4-(pyridin-3-yl)but-3-en-2-one

C

3-hydroxy-1-(3-pyridyl)-1-butanone

3-hydroxy-1-(3-pyridyl)-1-butanone

D

2'-deoxyguanosine 3'-(ethyl carbonate)
100044-90-4

2'-deoxyguanosine 3'-(ethyl carbonate)

Conditions
ConditionsYield
With pH 8 sodium phosphate buffer In water at 37℃; for 96h; Further byproducts given;
With pH 8 sodium buffer In water at 37℃; for 96h; Further byproducts given;
4-(carbethoxynitrosamino)-1-(3-pyridyl)-1-butanone
68743-68-0

4-(carbethoxynitrosamino)-1-(3-pyridyl)-1-butanone

9-(2'-deoxyribofuranosyl)guanine
961-07-9

9-(2'-deoxyribofuranosyl)guanine

A

(E)-4-(pyridin-3-yl)but-3-en-2-one
100021-45-2

(E)-4-(pyridin-3-yl)but-3-en-2-one

B

2'-deoxyguanosine 3'-(ethyl carbonate)
100044-90-4

2'-deoxyguanosine 3'-(ethyl carbonate)

C

2'-deoxyguanosine 5'-(ethyl carbonate)
100021-47-4

2'-deoxyguanosine 5'-(ethyl carbonate)

D

2'-deoxy-N-<1-methyl-3-oxo-3-(3-pyridyl)-propyl>guanosine

2'-deoxy-N-<1-methyl-3-oxo-3-(3-pyridyl)-propyl>guanosine

Conditions
ConditionsYield
With pH 8 sodium phosphate buffer In water at 37℃; for 96h; Further byproducts given;
triethylamine hydrochloride
554-68-7

triethylamine hydrochloride

9-(2'-deoxyribofuranosyl)guanine
961-07-9

9-(2'-deoxyribofuranosyl)guanine

N-isobutyryl deoxyguanosine
93635-99-5

N-isobutyryl deoxyguanosine

Conditions
ConditionsYield
With sodium methylate In methanol; hexane; N,N-dimethyl-formamide
9-(2'-deoxyribofuranosyl)guanine
961-07-9

9-(2'-deoxyribofuranosyl)guanine

cyclohexanylcarbonyl chloride
2719-27-9

cyclohexanylcarbonyl chloride

N2-cyclohexylcarbonyl-2'-deoxyguanosine
168466-00-0

N2-cyclohexylcarbonyl-2'-deoxyguanosine

Conditions
ConditionsYield
With chloro-trimethyl-silane; ammonium fluoride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; pyridine; methanol; ice-water; ethanol; water; toluene
9-(2'-deoxyribofuranosyl)guanine
961-07-9

9-(2'-deoxyribofuranosyl)guanine

A

C10H13N5O6

C10H13N5O6

B

C10H14N6O5

C10H14N6O5

Conditions
ConditionsYield
With rose bengal; ammonium chloride In aq. phosphate buffer at 22℃; pH=7.4; Irradiation;A 31 %Chromat.
B 62 %Chromat.
9-(2'-deoxyribofuranosyl)guanine
961-07-9

9-(2'-deoxyribofuranosyl)guanine

A

C10H13N5O6

C10H13N5O6

B

C10H14N6O5

C10H14N6O5

C

C10H14N6O5

C10H14N6O5

D

2,2-Diamino-4-((4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-ylamino)-2H-oxazol-5-one

2,2-Diamino-4-((4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-ylamino)-2H-oxazol-5-one

Conditions
ConditionsYield
With ammonium chloride; riboflavin In aq. phosphate buffer at 22℃; pH=7.4; Irradiation;A 11 %Chromat.
B 29 %Chromat.
C 11 %Chromat.
D 43 %Chromat.
9-(2'-deoxyribofuranosyl)guanine
961-07-9

9-(2'-deoxyribofuranosyl)guanine

A

C10H13N5O6

C10H13N5O6

B

C10H14N6O5

C10H14N6O5

C

C9H15N5O5*H(1+)

C9H15N5O5*H(1+)

Conditions
ConditionsYield
With sodium hexachloroiridate; ammonium chloride In aq. phosphate buffer at 22℃; pH=7.4; Irradiation;A 50 %Chromat.
B 42 %Chromat.
C 8 %Chromat.
9-(2'-deoxyribofuranosyl)guanine
961-07-9

9-(2'-deoxyribofuranosyl)guanine

C41H65N5O16

C41H65N5O16

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: N-Bromosuccinimide / water; acetonitrile
2: 1H-imidazole / N,N-dimethyl-formamide / 20 °C
3: diethylazodicarboxylate; triphenylphosphine / 1,4-dioxane / 50 °C
4: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 18 h / 40 °C / Inert atmosphere
5: hydrogenchloride / water; methanol / 20 °C
6: potassium carbonate / N,N-dimethyl-formamide / 50 °C
7: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C
View Scheme
9-(2'-deoxyribofuranosyl)guanine
961-07-9

9-(2'-deoxyribofuranosyl)guanine

C55H97N5O16Si2

C55H97N5O16Si2

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: N-Bromosuccinimide / water; acetonitrile
2: 1H-imidazole / N,N-dimethyl-formamide / 20 °C
3: diethylazodicarboxylate; triphenylphosphine / 1,4-dioxane / 50 °C
4: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 18 h / 40 °C / Inert atmosphere
5: hydrogenchloride / water; methanol / 20 °C
6: potassium carbonate / N,N-dimethyl-formamide / 50 °C
View Scheme
9-(2'-deoxyribofuranosyl)guanine
961-07-9

9-(2'-deoxyribofuranosyl)guanine

C21H37N5OSi2

C21H37N5OSi2

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: N-Bromosuccinimide / water; acetonitrile
2: 1H-imidazole / N,N-dimethyl-formamide / 20 °C
3: diethylazodicarboxylate; triphenylphosphine / 1,4-dioxane / 50 °C
4: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 18 h / 40 °C / Inert atmosphere
5: hydrogenchloride / water; methanol / 20 °C
View Scheme
9-(2'-deoxyribofuranosyl)guanine
961-07-9

9-(2'-deoxyribofuranosyl)guanine

C38H73N5O4Si4

C38H73N5O4Si4

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-Bromosuccinimide / water; acetonitrile
2: 1H-imidazole / N,N-dimethyl-formamide / 20 °C
3: diethylazodicarboxylate; triphenylphosphine / 1,4-dioxane / 50 °C
4: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 18 h / 40 °C / Inert atmosphere
View Scheme
9-(2'-deoxyribofuranosyl)guanine
961-07-9

9-(2'-deoxyribofuranosyl)guanine

C27H52BrN5O4Si3

C27H52BrN5O4Si3

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-Bromosuccinimide / water; acetonitrile
2: 1H-imidazole / N,N-dimethyl-formamide / 20 °C
3: diethylazodicarboxylate; triphenylphosphine / 1,4-dioxane / 50 °C
View Scheme
9-(2'-deoxyribofuranosyl)guanine
961-07-9

9-(2'-deoxyribofuranosyl)guanine

C22H40BrN5O4Si2

C22H40BrN5O4Si2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-Bromosuccinimide / water; acetonitrile
2: 1H-imidazole / N,N-dimethyl-formamide / 20 °C
View Scheme
9-(2'-deoxyribofuranosyl)guanine
961-07-9

9-(2'-deoxyribofuranosyl)guanine

C10H12BrN5O4

C10H12BrN5O4

Conditions
ConditionsYield
With N-Bromosuccinimide In water; acetonitrile

961-07-9Relevant articles and documents

Highly sequence selective photoreaction of 5-bromouracil-containing deoxyhexanucleotides

Sugiyama, Hiroshi,Tsutsumi, Yasushi,Saito, Isao

, p. 6720 - 6721 (1990)

-

Chemical composition and toxicity of Taiwanese betel quid extract

Wang,Su,Lii

, p. 135 - 144 (1999)

In this genotoxic study, the Ames Salmonella microsome test showed that an aqueous extract of betel quid did not induce mutagenicity in Salmonella typhimurium strains TA98 and TA100. Mammalian cell studies (Chinese hamster ovary K1 cell; CHO-K1 cell) revealed that only higher concentrations (100 and 1000μg/ml) of aqueous extract weekly increased the frequencies of sister-chromatid exchange (SCE) in the absence of S9. Animal (male Sprague-Dawley rat) studies showed that low-dose feeding (0.53g dry aqueous extract/kg diet) significantly increased the activities of glutathione (GSH) peroxidase and cytoplasmic glutathione S-transferase (cGST) of liver, high-dose feeding (26.5g dry aqueous extract/kg diet) lowered the contents of GSH and total glutathione. The effect of an aqueous extract of betel quid on the oxidation of 2'-deoxyguanosine (2'-dG) to 8-hydroxy-2'-deoxyguanosine (8-OH-dG) evaluated that this aqueous extract may act as a pro-oxidant at lower dosage and may be dependent on the iron ions in the model system. However, the aqueous extract of betel quid showed antioxidant activity at higher doses by the ability of the scavenging effect of the hydroxyl radicals. Copyright (C) 1999 Elsevier Science B.V.

Independent Generation and Reactivity of 2′-Deoxyguanosin- N1-yl Radical

Zheng, Liwei,Greenberg, Marc M.

, p. 8665 - 8672 (2020/07/03)

2′-Deoxyguanosin-N1-yl radical (dG(N1-H)?) is the thermodynamically favored one-electron oxidation product of 2′-deoxyguanosine (dG), the most readily oxidized native nucleoside. dG(N1-H)? is produced by the formal dehydration of a hydroxyl radical adduct of dG as well as by deprotonation of the corresponding radical cation. dG(N1-H)? were formed as a result of the indirect and direct effects of ionizing radiation, among other DNA damaging agents. dG(N1-H)? was generated photochemically (λmax = 350 nm) from an N-aryloxy-naphthalimide precursor (3). The quantum yield for photochemical conversion of 3 is ~0.03 and decreases significantly in the presence O2, suggesting that bond scission occurs from a triplet excited state. dG is formed quantitatively in the presence of excess β-mercaptoethanol. In the absence of a reducing agent, dG(N1-H)? oxidizes 3, decreasing the dG yield to ~50%. Addition of 8-oxo-7,8-dihydro-2′-deoxyguanosine (8-oxodGuo) as a sacrificial reductant results in a quantitative yield of dG and two-electron oxidation products of 8-oxodGuo. N-Aryloxy-naphthalimide 3 is an efficient and high-yielding photochemical precursor of dG(N1-H)? that will facilitate mechanistic studies on the reactivity of this important reactive intermediate involved in DNA damage.

Solid-phase synthesis and structural characterisation of phosphoroselenolate-modified DNA: A backbone analogue which does not impose conformational bias and facilitates SAD X-ray crystallography

Conlon, Patrick F.,Eguaogie, Olga,Wilson, Jordan J.,Sweet, Jamie S. T.,Steinhoegl, Julian,Englert, Klaudia,Hancox, Oliver G. A.,Law, Christopher J.,Allman, Sarah A.,Tucker, James H. R.,Hall, James P.,Vyle, Joseph S.

, p. 10948 - 10957 (2019/12/23)

Oligodeoxynucleotides incorporating internucleotide phosphoroselenolate linkages have been prepared under solid-phase synthesis conditions using dimer phosphoramidites. These dimers were constructed following the high yielding Michaelis-Arbuzov (M-A) reaction of nucleoside H-phosphonate derivatives with 5′-deoxythymidine-5′-selenocyanate and subsequent phosphitylation. Efficient coupling of the dimer phosphoramidites to solid-supported substrates was observed under both manual and automated conditions and required only minor modifications to the standard DNA synthesis cycle. In a further demonstration of the utility of M-A chemistry, the support-bound selenonucleoside was reacted with an H-phosphonate and then chain extended using phosphoramidite chemistry. Following initial unmasking of methyl-protected phosphoroselenolate diesters, pure oligodeoxynucleotides were isolated using standard deprotection and purification procedures and subsequently characterised by mass spectrometry and circular dichroism. The CD spectra of both modified and native duplexes derived from self-complementary sequences with A-form, B-form or mixed conformational preferences were essentially superimposable. These sequences were also used to study the effect of the modification upon duplex stability which showed context-dependent destabilisation (-0.4 to-3.1 °C per phosphoroselenolate) when introduced at the 5′-Termini of A-form or mixed duplexes or at juxtaposed central loci within a B-form duplex (-1.0 °C per modification). As found with other nucleic acids incorporating selenium, expeditious crystallisation of a modified decanucleotide A-form duplex was observed and the structure solved to a resolution of 1.45 ?. The DNA structure adjacent to the modification was not significantly perturbed. The phosphoroselenolate linkage was found to impart resistance to nuclease activity.

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