α-Methyl-γ-hydroxy-1,N2-propano-2'-deoxyguanosine (Mixture of DiastereoMers)

Base Information

• Chemical Name: α-Methyl-γ-hydroxy-1,N2-propano-2'-deoxyguanosine (Mixture of DiastereoMers)
• CAS No.: 132014-87-0
• Molecular Formula: C₁₄H₁₉N₅O₅
• Molecular Weight: 337.335
• Mol file: 132014-87-0.mol

Synonyms:8-hydroxy-3-(4-hydroxy-5-hydroxymethyl-tetra-hydrofuran-2-yl)-6-methyl-5,6,7,8-tetrahydro-3H-1,3,4,5,8a-pentaaza-cyclopenta[b]naphthalen-9-one

Chemical Property of α-Methyl-γ-hydroxy-1,N2-propano-2'-deoxyguanosine (Mixture of DiastereoMers)

Chemical Property:

• Melting Point: 135-137°C
• Boiling Point: 724.7±70.0 °C(Predicted)
• PKA: 11.80±0.40(Predicted)
• Density: 1.93±0.1 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• Solubility.: Methanol (Slightly), Water (Slightly)

Purity/Quality:

98%min ^*data from raw suppliers

α-Methyl-γ-hydroxy-1,N2-propano-2’-deoxyguanosine(MixtureofDiastereomers) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: A genotoxi crotonaldehyde. A genotoxic cyclic adduct of 2''-deoxyguanosine with crotonaldehyde. Histones accelerate the cyclic 1,N2-propanoguanine adduct-formation of DNA by the primary metabolite of alcohol and carcinogenic crotonaldehyde.

Technology Process of α-Methyl-γ-hydroxy-1,N2-propano-2'-deoxyguanosine (Mixture of DiastereoMers)

There total 11 articles about α-Methyl-γ-hydroxy-1,N2-propano-2'-deoxyguanosine (Mixture of DiastereoMers) 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: 95.0%

2'-Deoxyguanosine (961-07-9) + crotonaldehyde (123-73-9,4170-30-3) → 8-hydroxy-3-(4-hydroxy-5-hydroxymethyl-tetra-hydrofuran-2-yl)-6-methyl-5,6,7,8-tetrahydro-3H-1,3,4,5,8a-pentaaza-cyclopenta[b]naphthalen-9-one (132014-87-0)

Guidance literature:

With phosphate buffer; L-arginine; at 50 ℃; for 1h; pH=8.5;

DOI:10.1016/S0040-4020(02)01047-5

Reference yield: 92.0%

2'-Deoxyguanosine (961-07-9) + acetaldehyde (75-07-0,9002-91-9) → trans-Crotonaldehyde (123-73-9,4170-30-3) + 8-hydroxy-3-(4-hydroxy-5-hydroxymethyl-tetra-hydrofuran-2-yl)-6-methyl-5,6,7,8-tetrahydro-3H-1,3,4,5,8a-pentaaza-cyclopenta[b]naphthalen-9-one (132014-87-0)

Guidance literature:

With L-arginine; In phosphate buffer; at 37 ℃; for 8h; pH=8.0;

DOI:10.1016/S0040-4039(02)01530-7

Reference yield:

acetaldehyde (75-07-0,9002-91-9) + calf thymus DNA → 3-(2-deoxyribos-1-yl)-5,6,7,8-tetrahydro-8-(N2-deoxyguanosyl)-6-methylpyrimido[1,2-a]purine-10(3H)one + N2-ethyl-2'-deoxyguanosine + 8-hydroxy-3-(4-hydroxy-5-hydroxymethyl-tetra-hydrofuran-2-yl)-6-methyl-5,6,7,8-tetrahydro-3H-1,3,4,5,8a-pentaaza-cyclopenta[b]naphthalen-9-one (132014-87-0) + N2-(2,6-dimethyl-1,3-dioxan-4-yl)deoxyguanosin

Guidance literature:

acetaldehyde; calf thymus DNA; In phosphate buffer; at 37 ℃; for 96h; pH=7.0;

With sodium cyanoborohydride; at 20 - 37 ℃;

With phosphodiesterase; DNase I; alkaline phosphatase; at 37 ℃; for 70h; pH=7.0;

DOI:10.1021/tx000118t

upstream raw materials:

trans-Crotonaldehyde

2'-Deoxyguanosine

(R)-3-Hydroxybutanal

crotonaldehyde

Downstream raw materials:

2'-Deoxyguanosine

Refernces

• 1、 Wang,McIntee,Cheng,Shi,Villalta,Hecht. "Reactions of 2,6-dimethyl-1,3-dioxane-4-ol (aldoxane) with deoxyguanosine and DNA". . p. 1025 - 1032. Retrieved 2001.
• 2、 Sako, Magoichi,Yaekura, Isamu. "A convenient preparative method for the 1,N2-cyclic adducts of guanine nucleosides and nucleotides with crotonaldehyde". . p. 8413 - 8416. Retrieved 2002.
• 3、 Sako, Magoichi,Yaekura, Isamu,Deyashiki, Yoshihiro. "Smooth and selective formation of the cyclic 1,N2-propano adducts in the reactions of guanine nucleosides and nucleotides with acetaldehyde". . p. 6701 - 6703. Retrieved 2007/10/03.