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:
Molecular Weight:
286.67
EC Number:
226-438-4
UNSPSC Code:
41106305
PubChem Substance ID:
Beilstein/REAXYS Number:
40573
MDL number:
Assay:
≥98% (HPLC)
Form:
powder
Solubility:
DMF: 49-51 mg/mL, clear, colorless to faintly yellow
Storage temp.:
−20°C
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
SMILES string
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(Cl)ncnc23
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
InChI key
XHRJGHCQQPETRH-KQYNXXCUSA-N
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.
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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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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
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
J Alonso et al.
International journal of peptide and protein research, 34(1), 66-69 (1989-07-01)
The reaction of ribonuclease A with either 6-chloropurine riboside 5'-monophosphate or the corresponding nucleoside yields one derivative, with the reagent covalently bound to the alpha-amino group of Lys-1, called derivative II and derivative E, respectively. We studied by means of