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Merck
CN

C8276

6-Chloropurine riboside

Synonym(s):

6-Chloropurine-9-β-D-ribofuranoside

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About This Item

Empirical Formula (Hill Notation):
C10H11ClN4O4
CAS Number:
5399-87-1
Molecular Weight:
286.67
EC Number:
226-438-4
UNSPSC Code:
41106305
PubChem Substance ID:
24893040
Beilstein/REAXYS Number:
40573
MDL number:
MFCD00005738
Assay:
≥98% (HPLC)
Form:
powder
Solubility:
DMF: 49-51 mg/mL, clear, colorless to faintly yellow
Storage temp.:
−20°C

Key Documents

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InChI key

XHRJGHCQQPETRH-KQYNXXCUSA-N

InChI

1S/C10H11ClN4O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2/t4-,6-,7-,10-/m1/s1

SMILES string

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(Cl)ncnc23

assay

≥98% (HPLC)

form

powder

mp

158-162 °C (dec.) (lit.)

solubility

DMF: 49-51 mg/mL, clear, colorless to faintly yellow

storage temp.

−20°C

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Application

6-Chloropurine riboside is used to study the kinetics and substrate specificity of adenosine deaminase. 6-Chloropurine riboside is benzoylated to facilitate synthesis of nucleoside derivatives such as 9-(2,3-Di-deoxy-2-fluoro-β-D-threo-pentofuranosyl)adenine. 6-Chloropurine riboside, especially after phosphorylation to NMP, NDP or NTP, is used as a purine substrate analogue in studies with enzymes such as Inosine monophosphate dehydrogenase (IMPDH); bacteriophage T4 RNA-ligase (EC 6.5.1.3) and pancreatic fibonuclease A.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000480511
0000480511
0000462247
0000462247
0000104204

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B A Iuodka et al.
Biokhimiia (Moscow, Russia), 58(6), 857-865 (1993-06-01)
The NTP binding site of bacteriophage T4 RNA-ligase (EC 6.5.1.3) was studied using several ATP analogs modified in the purine moiety of the nucleotide at positions 1, 2, 6 and 8: adenosine-N'-oxide 5'-triphosphate (I), 6-chloropurine riboside 5'-triphosphate (II), 6-mercaptopurine riboside
L S Singh et al.
Molecular and cellular biochemistry, 204(1-2), 127-134 (2000-03-16)
Adenosine deaminase (ADA) was isolated from small intestine of mice and purified to utmost homogeneity. SDS-PAGE of purified ADA gave a molecular weight of 41 kDa. Western blot analyses gave a single reactive band at 41 kDa and the other
R M Richardson et al.
Biochimica et biophysica acta, 953(1), 70-78 (1988-03-02)
When the reaction of bovine pancreatic ribonuclease A with 6-chloropurine riboside 5'-monophosphate was carried out in the presence of several natural mononucleotides, a decrease of 25-75% was found in the amount of the reaction product derivative II (the main product
Cintia W Rivero et al.
Bioorganic & medicinal chemistry letters, 22(19), 6059-6062 (2012-09-11)
This work describes the application of thermophilic microorganisms for obtaining 6-halogenated purine nucleosides. Biosynthesis of 6-chloropurine-2'-deoxyriboside and 6-chloropurine riboside was achieved by Geobacillus stearothermophilus CECT 43 with a conversion of 90% and 68%, respectively. Furthermore, the selected microorganism was satisfactorily
Shigetada Kozai et al.
Nucleosides, nucleotides & nucleic acids, 22(5-8), 779-781 (2003-10-21)
A new method to introduce a benzyl group onto the 2'-OH of purine ribonucleoside is described. Thus, 6-chloropurine 3'-O-benzoylriboside and its 5'-O-trityl congener were condensed with benzyl alcohol using the Mitsunobu reaction to give the 2'-O-benzyl derivative. The yields were
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