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N8016

Sigma-Aldrich

2-Nitrophenyl β-D-glucopyranoside

≥99% (TLC), powder

Synonym(s):

2-Nitrophenyl-beta-D-glucopyranoside, o-NPG

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About This Item

Empirical Formula (Hill Notation):
C12H15NO8
CAS Number:
2816-24-2
Molecular Weight:
301.25
Beilstein:
92206
EC Number:
220-568-5
MDL number:
MFCD00065048
UNSPSC Code:
12352204
PubChem Substance ID:
24897848
NACRES:
NA.28

product name

2-Nitrophenyl β-D-glucopyranoside, powder

Assay

≥99% (TLC)

Quality Level

300

form

powder

solubility

water: 50 mg/mL

storage temp.

−20°C

SMILES string

OC[C@H]1O[C@@H](Oc2ccccc2[N+]([O-])=O)[C@H](O)[C@@H](O)[C@@H]1O

InChI

1S/C12H15NO8/c14-5-8-9(15)10(16)11(17)12(21-8)20-7-4-2-1-3-6(7)13(18)19/h1-4,8-12,14-17H,5H2/t8-,9-,10+,11-,12-/m1/s1

InChI key

KUWPCJHYPSUOFW-RMPHRYRLSA-N

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Application

2-Nitrophenyl β-D-glucopyranoside has been used as a substrate for glucosidase in protein assay and in a colorimetric assay to determine protein stability.

Biochem/physiol Actions

2-Nitrophenyl β-D-glucopyranoside serves as an artificial substrate for glucosidase.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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L M Hernandez et al.
FEBS letters, 161(2), 190-194 (1983-09-19)
Accumulation and secretion of beta-glucanases have been studied in vivo by using a thermosensitive secretory mutant of Saccharomyces cerevisiae blocked at the endoplasmic reticulum level (sec 18-1). When incubated at the restrictive temperature no accumulation of active glucanases was observed.
Toshihiro Ohta et al.
Mutagenesis, 21(4), 255-260 (2006-06-17)
Thermus thermophilus is an extremely thermophilic eubacterium that grows optimally at 70-75 degrees C. Because the frequency of DNA damage, such as deamination, depurination and single-strand breaks, increases as the temperature rises, the regulation of expression as well as the
M Moracci et al.
Biochemistry, 37(49), 17262-17270 (1998-12-23)
The beta-glycosidase from the hyperthermophilic Archaeon Sulfolobus solfataricus hydrolyzes beta-glycosides following a retaining mechanism based upon the action of two amino acids: Glu387, which acts as the nucleophile of the reaction, and Glu206, which acts as the general acid/base catalyst.
J Feldwisch et al.
The Biochemical journal, 302 ( Pt 1), 15-21 (1994-08-15)
We isolated membrane vesicles from maize (Zea mays L.) coleoptiles and identified in these vesicles a 58 kDa (pm58) and a 60 kDa (pm60) protein by photoaffinity labelling with 5-azido-[7-3H]indole-3-acetic acid ([3H]N3IAA). Photoaffinity labelling was effectively competed for by auxins
J H Lebbink et al.
Biochemistry, 39(13), 3656-3665 (2000-03-29)
The beta-glucosidase from the hyperthermophilic archaeon Pyrococcus furiosus (CelB) is the most thermostable and thermoactive family 1 glycosylhydrolase described to date. To obtain more insight in the molecular determinants of adaptations to high temperatures and study the possibility of optimizing
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