2-Amino-6-chloropurine Riboside Chemical Properties

Melting point:

165-167 °C (dec.)(lit.)

Boiling point:

729.9±70.0 °C(Predicted)

Density 

1.8359 (rough estimate)

refractive index 

-38 ° (C=0.1, H2O)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

solubility 

DMSO, Methanol

form 

Powder

pka

13.05±0.70(Predicted)

color 

White to Off-white

InChIKey

TXWHPSZYRUHEGT-ACJOCUEISA-N

CAS DataBase Reference

2004-07-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-36-26

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29349990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

2-Amino-6-chloropurine Riboside Usage And Synthesis

Chemical Properties

Colourless Crystalline Solid

Uses

2-Amino-6-chloropurine riboside (1) is a a novel class of inhibitors of endogenous protein degradation for the preparation of a number of important purine nucleoside derivatives. For example, 6-thioguanosine 2 and 6-selenoguanosine 3 were prepared from a reaction of 1 and the corresponding sodium thiosulfate or potassium selenosulfate.1) 18O-labeled guanosine 4 was incubated from 1 with adenosine deaminase in (18O)-water.2) 2-Amino-6-ethoxypurine riboside 5 and 2-amino-N6-amino-N6-methyladenosine 6 were prepared by treatment of 1 with nucleophiles, sodium ethoxide and methylhydrazine, respectively.3,4) 2-Amino-N6-substituted purine analogues, as typified by 6, were reported as anti-malarial active compounds.

Synthesis

GENERAL STEPS: (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2-amino-6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (1.56 g, 3.64 mmol) was dissolved in acetone (10 mL), phosphate buffer (58 mL, pH 8) and Novozyme (1.6 g) were added. The reaction mixture was stirred at 60°C for 8 days. After completion of the reaction, the enzyme was removed by filtration and washed with ethanol (50 mL) and acetone (50 mL). The filtrate was concentrated under reduced pressure and the resulting crude product was purified by silica gel column chromatography (eluent: CH2Cl2:MeOH, 85:15) to afford (2R,3R,4S,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (0.61 g, 55% yield) as a light blue powder.1H NMR ( 400 MHz, DMSO-d6) δ 8.38 (s, 1H, H-8), 6.99 (s, 1H, NH2), 5.81 (d, J = 5.80 Hz, 1H, H-1'), 5.49 (br s, 1H, OH-2'), 5.19 (br s, 1H, OH-3'), 5.05 (t, J = 5.24 Hz, 1H, OH -5'), 4.47 (t, J = 4.85 Hz, 1H, H-2'), 4.20-4.02 (m, 1H, H-3'), 3.90 (q, J = 3.98 Hz, 1H, H-4'), 3.69-3.60 (m, 1H, H2-5'), 3.59-3.52 (m, 1H, H2-5'); 13C NMR (100 MHz, DMSO-d6) δ 160.5, 154.7, 150.2, 141.9, 124.2, 87.4, 86.0, 74.2, 70.9, 61.9; high resolution ES-MS m/z 302.0649 ([M + H]+, C10H1335ClN5O4 calculated value 302.0651).

References

[1] A. JANKOWSKI L. T D Wise. Sodium Thiosulfate and Potassium Selenosulfate as Reagents to Prepare Thio-and Selenopurine Nucleosides[J]. Nucleosides, Nucleotides & Nucleic Acids, 1989, 8 1: 339-348. DOI:10.1080/07328318908054179.
[2] SUNDEEP RAYAT. 5-Cyanoimino-4-oxomethylene-4,5-dihydroimidazole and 5-Cyanoamino-4-imidazolecarboxylic Acid Intermediates in Nitrosative Guanosine Deamination: Evidence from 18O-Labeling Experiments[J]. Journal of the American Chemical Society, 2004, 126 32: 9960-9969. DOI:10.1021/ja049835q.
[3] MORRIS J. ROBINS. Nucleic acid related compounds. 114. Synthesis of 2,6-(disubstituted)purine 2′,3′-dideoxynucleosides and selected cytotoxic, anti-hepatitis b, and adenosine deaminase substrate activities[J]. Journal of Heterocyclic Chemistry, 2009, 38 6: 1297-1306. DOI:10.1002/jhet.5570380609.
[4] KATHLEEN TOO . Anti-malarial activity of N6-modified purine analogues[J]. Bioorganic & Medicinal Chemistry, 2007, 15 16: Pages 5551-5562. DOI:10.1016/j.bmc.2007.05.038.
[5] ALICJA STACHELSKA-WIERZCHOWSKA. Tri-Cyclic Nucleobase Analogs and their Ribosides as Substrates of Purine-Nucleoside Phosphorylases. II Guanine and Isoguanine Derivatives.[J]. Molecules, 2019, 24 8. DOI:10.3390/molecules24081493.
[6] SHIH-HSI CHU Ming Y C Chyng Yann Shiue. Synthesis and cytotoxicity of 6-selenopurine arabinoside and related compounds[J]. Journal of pharmaceutical sciences, 1975, 64 8: 1343-1346. DOI:10.1002/jps.2600640818.

2-Amino-6-chloropurine Riboside(2004-07-1)Related Product Information

• PUROMYCIN AMINONUCLEOSIDE
• Adenosine
• Guanine
• Guanosine
• Guanosine 5'-monophosphate disodium salt
• Glycine
• 6-Chloroguanine
• 6-Chloropurine
• Acyclovir
• Ribavirin
• 6-Chloropurine ribonucleoside
• 3-Aminophenol
• 6-Aminocaproic acid
• 6-Thioguanine
• NUCLEOSIDE PHOSPHORYLASE BACTERIAL
• 5'-Guanylic acid
• 6-O-Methyl-guanine
• Tris(hydroxymethyl)aminomethane