2'-Deoxyguanosine monohydrate

Base Information

• Chemical Name: 2'-Deoxyguanosine monohydrate
• CAS No.: 961-07-9
• Molecular Formula: C10H13N5O4
• Molecular Weight: 267.244
• Hs Code.: 29349990
• Mol file: 961-07-9.mol

Synonyms:2'-Deoxyguanosine;9H-Purin-6-ol, 2-amino-9-(2-deoxy-9-beta-D-ribofuranosyl)-;Guanine deoxyriboside;

Chemical Property of 2'-Deoxyguanosine monohydrate

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 300 °C
• Refractive Index: -42 ° (C=0.2, 1mol/L NaOH)
• Boiling Point: 725.475 °C at 760 mmHg
• PKA: 9?+-.0.20(Predicted)
• Flash Point: 392.553 °C
• PSA: 148.51000
• Density: 2.085 g/cm³
• LogP: -1.14060
• Storage Temp.: Store at RT.
• Solubility.: NH4OH 1 M: 50 mg/mL, clear to very faintly turbid, yellow t
• Water Solubility.: Slightly soluble in water.

Purity/Quality:

98% ^*data from raw suppliers

2''-Deoxyguanosine ^*data from reagent suppliers

Safty Information:

• Statements: 20/21/22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• 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.

Technology Process of 2'-Deoxyguanosine monohydrate

There total 137 articles about 2'-Deoxyguanosine monohydrate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

5'-d(AGTAT[5-ethynyl-U]GACCTA)-3' → 2'-deoxycytidine (959326-89-7) + 2'-Deoxyguanosine (961-07-9) + 2'-deoxy-5-ethynyluridine (61135-33-9) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) + 2'-deoxy-D-adenosine (958-09-8,7005-15-4)

Guidance literature:

With tris hydrochloride; alkaline phosphatase; snake venom phosphodiesterase; at 37 ℃; pH=8.3; Enzymatic reaction;

DOI:10.1002/chem.201001572

Reference yield:

calf thymus DNA, γ-irradiated → 8-oxo-7,8-dihydro-2'-deoxyguanosine (31077-24-4,62471-63-0) + (5'S)-5',8-cyclo-2'-deoxyguanosine (105929-27-9) + 2'-Deoxyguanosine (961-07-9) + 7,8-dihydro-8-oxo-2'-deoxyguanosine (88847-89-6) + (5'S)-5',8-cyclo-2'-deoxyadenosine (117182-88-4) + (5'R)-5',8-cyclo-2'-deoxyadenosine + (5'R)-5',8-cyclo-2'-deoxyguanosine + 2'-Deoxycytidine (951-77-9) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) + 2'-deoxy-D-adenosine (958-09-8,7005-15-4)

Guidance literature:

calf thymus DNA, γ-irradiated; With DNase II; Penicillium citrium nuclease P₁; phosphodiesterase II; 9-erythro-(2-hydroxy-3-n-nonyl)adenine hydrochloride; at 37 ℃; for 2h; pH=6; aq. buffer; Enzymatic reaction;

With phosphodiesterase I from Crotalus adamentus venom; alkaline phosphatase; at 37 ℃; for 2h; pH=8; aq. buffer; Enzymatic reaction;

With DNase II; Penicillium citrium nuclease P₁; phosphodiesterase II; at 37 ℃; for 2h; pH=6; optical yield given as %de; aq. buffer; Enzymatic reaction;

DOI:10.1039/c004531d

Reference yield:

N2-(tetrahydrofuran-2-yl)deoxyguanosine (163088-94-6) → 2-hydroxytetrahydrofuran (5371-52-8) + 2'-Deoxyguanosine (961-07-9)

Guidance literature:

at 100 ℃; for 1h; pH=7.0; Product distribution;

DOI:10.1021/tx00046a016

upstream raw materials:

2-deoxy–α-D-ribose 1-phosphate

guanine

2'-Deoxycytidine

1-methylguanidine

Downstream raw materials:

2'-deoxyguanosine 5'-monophosphate

2'-deoxyxanthosine

2'-deoxy-D-adenosine

3',5'-O-dibutyryl 2'-deoxyguanosine

Refernces

Synthesis of 8-[¹⁸O]hydroxy-2'-deoxyguanosine

10.1002/jlcr.2580340213

The research aims to develop a method for synthesizing 8-[18O]hydroxy-2'-deoxyguanosine (8-[18O]OH-dG) to be used as an internal standard for the quantification of 8-hydroxy-2'-deoxyguanosine (oh8dG) by GC-MS. oh8dG is a significant marker of oxidatively damaged DNA, which is relevant in carcinogenesis, mutagenesis, and toxicology. The synthesis process involves several steps, starting with the bromination of 2'-deoxyguanosine to produce 8-bromo-2'-deoxyguanosine, followed by the conversion to 8-[18O]benzyloxy-2'-deoxyguanosine using the sodium salt of [18O]benzyl alcohol, and finally, the reduction to 8-[18O]hydroxy-2'-deoxyguanosine through catalytic transfer hydrogenation. Key chemicals used include 2'-deoxyguanosine, bromine, ethyl benzimidate hydrochloride, H218O, LiAlH4, sodium hydride, and palladium on carbon. The overall yield of 8-[18O]OH-dG from H218O was approximately 4%, with an isotopic purity of 93.4 atom% as determined by GC-MS. The synthesized compound meets the required purity standards for its intended application as an internal standard in the analysis of oh8dG extracted from in vivo DNA and urine.

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