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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)

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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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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