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852481

Sigma-Aldrich

6-Chloropurine riboside

99%

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
Beilstein/REAXYS Number:
40573
EC Number:
226-438-4
MDL number:
MFCD00005738
UNSPSC Code:
12352123
PubChem Substance ID:
24888323
NACRES:
NA.22

assay

99%

form

powder

mp

158-162 °C (dec.) (lit.)

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

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Application

For a review of the geochemical and biological effects of this riboside, see Adv. Exp. Med. Biol. .

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Chem. Abstr., 106, 95594r-95594r (1987)
Selection of purine nucleoside analogs based on multiple biological and biochemical parameters.
M J Noujaim et al.
Advances in experimental medicine and biology, 195 Pt B, 165-169 (1986-01-01)
Masahiro Ikejiri et al.
Bioorganic & medicinal chemistry, 15(22), 6882-6892 (2007-09-04)
On the basis of our previous study on antiviral agents against the severe acute respiratory syndrome (SARS) coronavirus, a series of nucleoside analogues whose 5'-hydroxyl groups are masked by various protective groups such as carboxylate, sulfonate, and ether were synthesized
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
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
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