38819-10-2

Basic information

• Product Name: 9-(BETA-D-ARABINOFURANOSYL)GUANINE
• Synonyms: 2-AMino-9-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one;9-beta-D-Arabinofuranosylguanine Hydrate;Arabinoguanosine;Araguanosine;ara-Guanosine;Guanine arabinoside;-D-Arabinofuranosylguanine Hydrate;9-&beta
• CAS NO: 38819-10-2
• Molecular Formula: C₁₀H₁₃N₅O₅
• Molecular Weight: 283.24
• Mol File: 38819-10-2.mol
• Article Data: 15

Chemical Properties

• Melting Point: 225°C(lit.)
• Boiling Point: 775.9 °C at 760 mmHg
• Flash Point: 423.1 °C
• Appearance: Slightly off white to white powder
• Density: 2.25 g/cm³
• Vapor Pressure: 2.44E-25mmHg at 25°C
• Refractive Index: 1.955
• Storage Temp.: 2-8°C
• Solubility: DMSO: >10mg/mL
• PKA: 9?+-.0.20(Predicted)
• CAS DataBase Reference: 9-(BETA-D-ARABINOFURANOSYL)GUANINE(CAS DataBase Reference)
• NIST Chemistry Reference: 9-(BETA-D-ARABINOFURANOSYL)GUANINE(38819-10-2)
• EPA Substance Registry System: 9-(BETA-D-ARABINOFURANOSYL)GUANINE(38819-10-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• WGK Germany: 3
• RTECS: MF8301000
• Hazardous Substances Data: 38819-10-2(Hazardous Substances Data)

Usage

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.

Definition

ChEBI: A purine nucleoside in which guanine is attached to arabinofuranose via a beta-N9-glycosidic bond. It inhibits DNA synthesis and causes cell death.

InChI:InChI=1/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6+,9-/m1/s1

Upstream product

• 34079-68-0 2,6-diamino-9-(β-D-arabinofuranosyl)-purine 
• 129835-17-2 9-[3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]guanine 
• 35085-24-6 2-amino-6-chloro-9-(2,3,5-triphenylmethoxy-β-D-arabinofuranosyl)purine 
• 3083-77-0 araU 
• 118-00-3 G 
• 73-40-5 2-amino-6-hydroxypurine 
• 148313-05-7 9-<β-D-arabinofuranosyl>-O⁶-<2-(4-nitrophenyl)ethyl>guanine 
• 99691-93-7 8-Carbamoyl-2'-O-p-toluenesulfonyladenosine 
• 120595-74-6 2-Amino-6-chloro-9-β-D-arabinofuranosylpurine 
• 69304-44-5 3',5'-O-1,1,3,3-tetraisopropyldisiloxan-1,3-diyl-guanosine 
• 13368-14-4 2-Chloro-6-hydroxypurine 
• 70284-18-3 9-β-D-arabinofuranosyl-2-chlorohypoxanthine 
• 73-40-5 2-amino-1,9-dihydro-6H-purin-6-one 
• 5536-17-4 arabinosyl adenine 

Downstream Products

• 74491-89-7 9-(2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl)guanine 
• 80681-25-0 2’-fluoro-N2-isobutyryl-2’-deoxyguanosine 
• 78842-13-4 2'-deoxy-2'-fluoroguanosine 
• 146954-68-9 N²-isobutyryl-9-(3,5-di-O-tetrahydropyran-2-yl-β-D-arabinofuranosyl)guanine 
• 146954-69-0 N²-isobutyryl-9-(2-fluoro-3,5-di-O-tetrahydropyran-2-yl-β-D-arabinofuranosyl)guanine 
• 200404-37-1 Trifluoro-methanesulfonic acid (2R,3S,4R,5R)-2-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-4-(tetrahydro-pyran-2-yloxy)-5-(tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-3-yl ester 
• 160684-49-1 Acetic acid (2R,3S,4R,5R)-4-hydroxy-5-hydroxymethyl-2-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester 
• 160684-47-9 N2-isobutyryl-9-[3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]guanine 
• 160684-48-0 Acetic acid (2R,3S,3aR,9aR)-2-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl ester 
• 42495-71-6 dimethylgold(III) chloride 
• 7013-16-3 9-(β-D-arabinofuranosyl)-9H-purin-6(1H)-one 
• 5536-17-4 arabinosyl adenine 
• 146-78-1 Fludarabine 
• 10147-12-3 9-(β-D-arabinofuranosyl)-2-chloroadenine 

Relevant articles and documents

Synthesis of 2'-iodo- and 2'-bromo-ATP and GTP analogues as potential phasing tools for X-ray crystallography

Ara-adenosine (adenine 9-β-D-arabinofuranoside) and ara-guanosine (guanine 9-β-D-arabinofuranoside) are converted into 2' halogenated ATP and GTP analogues by triflation and subsequent inversion of configuration at C- 2'. For the commercially unavailable ara-guanosine a short synthesis starting from guanosine is presented. The nucleotide analogues could serve for the preparation of heavy atom derivatives of ATP- and GTP-binding proteins useful for protein crystal structure determination by MIR/MAD phasing.

MODIFIED OLIGONUCLEOTIDES AND METHODS OF USE IN TAUOPATHIES

Oligonucleotides comprising modifications at the 2' and/or 3' positions(s) along with methods of 5 making and use against Alzheimer disease and other tauopathies are disclosed.

Enzymatic Synthesis of Therapeutic Nucleosides using a Highly Versatile Purine Nucleoside 2’-DeoxyribosylTransferase from Trypanosoma brucei

The use of enzymes for the synthesis of nucleoside analogues offers several advantages over multistep chemical methods, including chemo-, regio- and stereoselectivity as well as milder reaction conditions. Herein, the production, characterization and utilization of a purine nucleoside 2’-deoxyribosyltransferase (PDT) from Trypanosoma brucei are reported. TbPDT is a dimer which displays not only excellent activity and stability over a broad range of temperatures (50–70 °C), pH (4–7) and ionic strength (0–500 mM NaCl) but also an unusual high stability under alkaline conditions (pH 8–10). TbPDT is shown to be proficient in the biosynthesis of numerous therapeutic nucleosides, including didanosine, vidarabine, cladribine, fludarabine and nelarabine. The structure-guided replacement of Val11 with either Ala or Ser resulted in variants with 2.8-fold greater activity. TbPDT was also covalently immobilized on glutaraldehyde-activated magnetic microspheres. MTbPDT3 was selected as the best derivative (4200 IU/g, activity recovery of 22 %), and could be easily recaptured and recycled for >25 reactions with negligible loss of activity. Finally, MTbPDT3 was successfully employed in the expedient synthesis of several nucleoside analogues. Taken together, our results support the notion that TbPDT has good potential as an industrial biocatalyst for the synthesis of a wide range of therapeutic nucleosides through an efficient and environmentally friendly methodology.

Synthesis of 9-β-d-arabinofuranosylguanine by combined use of two whole cell biocatalysts

Unlike the preparation of other purine nucleosides, transglycosylation from a pyrimidine nucleoside and guanine is difficult because of the low solubility of this base. Thus, another strategy, based on the coupled action of two whole cell biocatalyzed reactions, transglycosylation and deamination, was used. Enterobacter gergoviae and Arthrobacter oxydans were employed to synthesize 9-β-d-arabinofuranosylguanine (AraG), an efficient anti leukemic drug.