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A1269

Sigma-Aldrich

4-Aminophenyl β-D-glucopyranoside

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About This Item

Empirical Formula (Hill Notation):
C12H17NO6
CAS Number:
Molecular Weight:
271.27
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.25

assay

≥98% (TLC)

Quality Level

form

powder

optical activity

[α]/D -65.00 to -59.00°, c = 9.00-11.00 mg/mL in water

technique(s)

thin layer chromatography (TLC): suitable

solubility

water: 49.00-51.00 mg/mL, clear to slightly hazy, colorless to light yellow

storage temp.

−20°C

SMILES string

Nc1ccc(OC2OC(CO)C(O)C(O)C2O)cc1

InChI

1S/C12H17NO6/c13-6-1-3-7(4-2-6)18-12-11(17)10(16)9(15)8(5-14)19-12/h1-4,8-12,14-17H,5,13H2

InChI key

MIAKOEWBCMPCQR-UHFFFAOYSA-N

Application

P-Aminophenyl β-D-glucopyranoside is used to create derivitized agarose beads useful for the analysis of the surfaces of cancer cells. 4-Aminophenyl β-D-glucopyranoside is used to derivatize biocompatible single-crystalline gold tabular nanoparticles, nanoprisms (NPRs) to improve their stability and cellular uptake.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

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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Maria R Khurrum et al.
Acta histochemica, 104(3), 217-223 (2002-10-23)
Standard histochemical analysis of cells and tissues generally involves procedures that utilize a relatively small number of probes such as dyes, and generally requires hours or days to process. Our laboratory has developed a novel method for histochemical surveys of
Beatriz Pelaz et al.
Langmuir : the ACS journal of surfaces and colloids, 28(24), 8965-8970 (2012-01-21)
The paper describes a novel and straightforward wet-chemical synthetic route to produce biocompatible single-crystalline gold tabular nanoparticles, herein called nanoprisms (NPRs) due to their characteristic shape. Besides the novelty of the method to produce NPRs with an unprecedented high yield
Reductive syntheses of p-aminophenyl-beta-D-glucoside and its conversion to beta-glucosyl Yariv reagent.
I Ganjian et al.
Analytical biochemistry, 246(1), 152-155 (1997-03-01)
M Naoi et al.
Journal of neurochemistry, 50(4), 1297-1301 (1988-04-01)
Rat clonal pheochromocytoma PC12h cells were found to bind beta-galactosidase modified with specific glycosides. The enzyme modified with p-aminophenyl beta-D-glucoside was most effectively bound to the cells, followed by alpha-D-mannoside and alpha-D-glucoside. The binding was dependent on the number of
Olivier Laczka et al.
Analytica chimica acta, 677(2), 156-161 (2010-09-15)
Two simple methodologies are compared for the detection of faecal contamination in water using amperometry at gold interdigitated microelectrodes. They rely on the detection of β-galactosidase (β-gal) by redox cycling amperometry of the p-aminophenol (PAP) produced by the enzyme from

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