9-(BETA-D-ARABINOFURANOSYL)GUANINE

Base Information

• Chemical Name: 9-(BETA-D-ARABINOFURANOSYL)GUANINE
• CAS No.: 38819-10-2
• Molecular Formula: C10H13 N5 O5
• Molecular Weight: 283.244
• Hs Code.: 29349990
• Mol file: 38819-10-2.mol

Synonyms:Guanine,9-b-D-arabinofuranosyl- (7CI,8CI);2-Amino-6-hydroxy-9-(b-D-arabinofuranosyl)purine; 9-b-D-Arabinofuranosylguanine; Araguanosine; Guanine arabinoside; NSC 76352;ara-Guanosine

Chemical Property of 9-(BETA-D-ARABINOFURANOSYL)GUANINE

Chemical Property:

• Appearance/Colour: Slightly off white to white powder
• Vapor Pressure: 2.44E-25mmHg at 25°C
• Melting Point: 225°C(lit.)
• Refractive Index: 1.955
• Boiling Point: 775.9 °C at 760 mmHg
• PKA: 9?+-.0.20(Predicted)
• Flash Point: 423.1 °C
• PSA: 159.51000
• Density: 2.25 g/cm³
• LogP: -2.10550
• Storage Temp.: 2-8°C
• Solubility.: DMSO: >10mg/mL

Purity/Quality:

99% ^*data from raw suppliers

Ara-G ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Description: Ara-G is an analog of the nucleoside guanosine and an active metabolite of nelarabine . Ara-G accumulates in T lymphoblasts and malignant T-lymphoid cells, where it is phosphorylated to produce ara-GTP and incorporated into the DNA. Ara-G inhibits DNA replication by 92% after 30 minutes when used at a concentration of 50 μM in CEM cells, which are used as a model for human T lymphoblasts. It also halts the cell cycle at the sub-G1 phase and induces apoptosis in CEM cells. Syngeneic bone marrow containing 6C3HED tumor cells treated with ara-G (100 mM) ex vivo prior to transplantation increases survival of lethally irradiated mice and induces reconstitution of lymphoid, myeloid, and erythroid cell linages.
• Uses: Ara-G is an inducer of apoptosis, inhibitor of DNA synthesis, an antimetabolite, and antineoplastic.

Technology Process of 9-(BETA-D-ARABINOFURANOSYL)GUANINE

There total 33 articles about 9-(BETA-D-ARABINOFURANOSYL)GUANINE 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: 100.0%

2,6-diamino-9-(β-D-arabinofuranosyl)-purine (34079-68-0) → 9-β-D-arabinofuranosylguanine (38819-10-2)

Guidance literature:

With adenosine deaminase; at 37 ℃; for 48h; Enzymatic reaction;

DOI:10.1016/j.bmcl.2009.05.106

Reference yield: 71.0%

2-Amino-6-chloro-9-β-D-arabinofuranosylpurine (120595-74-6) → 9-β-D-arabinofuranosylguanine (38819-10-2)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; for 6h; Heating;

DOI:10.1002/jhet.5570250653

Reference yield: 64.0%

9-<β-D-arabinofuranosyl>-O6-<2-(4-nitrophenyl)ethyl>guanine (148313-05-7) → 9-β-D-arabinofuranosylguanine (38819-10-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 24h; Ambient temperature;

DOI:10.1002/hlca.19940770203

upstream raw materials:

3',5'-O-1,1,3,3-tetraisopropyldisiloxan-1,3-diyl-guanosine

2-Amino-6-chloro-9-β-D-arabinofuranosylpurine

8-Carbamoyl-2'-O-p-toluenesulfonyladenosine

9-<β-D-arabinofuranosyl>-O⁶-<2-(4-nitrophenyl)ethyl>guanine

Downstream raw materials:

9-[2-Hydroxy-1-(2-hydroxy-1-hydroxymethyl-ethoxy)-ethyl]-2-imino-1,2,3,9-tetrahydro-purin-6-one

9-β-D-Arabinofuranosylguanine 5'-Monophosphate

S-methyl-L-cysteine

1-methylguanosine

Refernces

• 1、 Utagawa,Morisawa,Yamanaka,et al.. "Microbial synthesis of purine arabinosides and their biological activity". . p. 2167 - 2171. Retrieved 1985.
• 2、 -. "MODIFIED OLIGONUCLEOTIDES AND METHODS OF USE". Paragraph 0230. . Retrieved 2018/04/12.
• 3、 Nóbile, Matías,Médici, Rosario,Terreni, Marco,Lewkowicz, Elizabeth S.,Iribarren, Adolfo M.. "Use of Citrobacter koseri whole cells for the production of arabinonucleosides: A larger scale approach". . p. 2182 - 2188. Retrieved 2013/02/25.