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496812

Sigma-Aldrich

7-Allyl-7,8-dihydro-8-oxoguanosine

95%

Synonym(s):

Loxoribine

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About This Item

Empirical Formula (Hill Notation):
C13H17N5O6
CAS Number:
121288-39-9
Molecular Weight:
339.30
MDL number:
MFCD00867591
UNSPSC Code:
41106305
PubChem Substance ID:
24873084
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

100

assay

95%

optical activity

[α]21/D −32°, c = 1 in H2O

mp

227-230 °C (lit.)

SMILES string

NC1=NC2=C(N(CC=C)C(=O)N2[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C(=O)N1

InChI

1S/C13H17N5O6/c1-2-3-17-6-9(15-12(14)16-10(6)22)18(13(17)23)11-8(21)7(20)5(4-19)24-11/h2,5,7-8,11,19-21H,1,3-4H2,(H3,14,15,16,22)/t5-,7-,8-,11-/m1/s1

InChI key

VDCRFBBZFHHYGT-IOSLPCCCSA-N

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Related Categories

Application

Loxoribine is a selective toll-like receptor 7 (TLR7) agonist that activates immune cells and increases cytokine production.

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)

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Certificates of Analysis (COA)

Lot/Batch Number
MKBP0595V
MKBN8530V
05902JH
08628ES
06915AC

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Thomas A Russo et al.
Infection and immunity, 82(6), 2356-2367 (2014-03-26)
Hypervirulent (hypermucoviscous) Klebsiella pneumoniae (hvKP) strains are an emerging variant of "classical" K. pneumoniae (cKP) that cause organ and life-threatening infection in healthy individuals. An understanding of hvKP-specific virulence mechanisms that enabled evolution from cKP is limited. Observations by our
Laura M van Staalduinen et al.
Proceedings of the National Academy of Sciences of the United States of America, 111(14), 5171-5176 (2014-04-08)
The enzymes PhnY and PhnZ comprise an oxidative catabolic pathway that enables marine bacteria to use 2-aminoethylphosphonic acid as a source of inorganic phosphate. PhnZ is notable for catalyzing the oxidative cleavage of a carbon-phosphorus bond using Fe(II) and dioxygen
Eunna Choi et al.
Infection and immunity, 82(6), 2203-2210 (2014-03-20)
In order to survive inside macrophages, Salmonella produces a series of proteins encoded by genes within Salmonella pathogenicity island 2 (SPI-2). In the present study, we report that Fur, a central regulator of iron utilization, negatively controls the expression of
Hypoferremia of infection: a double-edged sword?
Kristen L Lokken et al.
Nature medicine, 20(4), 335-337 (2014-04-09)
Don-Kyu Kim et al.
Nature medicine, 20(4), 419-424 (2014-03-25)
In response to microbial infection, expression of the defensin-like peptide hepcidin (encoded by Hamp) is induced in hepatocytes to decrease iron release from macrophages. To elucidate the mechanism by which Salmonella enterica var. Typhimurium (S. typhimurium), an intramacrophage bacterium, alters
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