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N9376

Sigma-Aldrich

4-Nitrophenyl N-acetyl-β-D-glucosaminide

chromogenic, ≥99% (TLC), powder

Synonym(s):

4-Nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranoside

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$57.11
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$128.00
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$237.00
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$281.00

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Estimated to ship onJuly 31, 2025FromMILWAUKEE

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100 MG
$57.11
250 MG
$128.00
500 MG
$237.00
1 G
$281.00

About This Item

Empirical Formula (Hill Notation):
C14H18N2O8
CAS Number:
3459-18-5
Molecular Weight:
342.30
Beilstein/REAXYS Number:
96193
EC Number:
222-398-7
MDL number:
MFCD00063696
UNSPSC Code:
12352204
PubChem Substance ID:
24897896
NACRES:
NA.32

$57.11

List Price$66.80Save 15%
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Estimated to ship onJuly 31, 2025FromMILWAUKEE

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Product Name

4-Nitrophenyl N-acetyl-β-D-glucosaminide, ≥99% (TLC)

assay

≥99% (TLC)

form

powder

impurities

≤0.05% Free p-nitrophenol

solubility

water: 5 mg/mL, clear, colorless to very faintly yellow

storage temp.

−20°C

SMILES string

CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1Oc2ccc(cc2)[N+]([O-])=O

InChI

1S/C14H18N2O8/c1-7(18)15-11-13(20)12(19)10(6-17)24-14(11)23-9-4-2-8(3-5-9)16(21)22/h2-5,10-14,17,19-20H,6H2,1H3,(H,15,18)/t10-,11-,12-,13-,14-/m1/s1

InChI key

OMRLTNCLYHKQCK-DHGKCCLASA-N

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Application

N-acetyl-β-D-glucosaminidase (NAG) has been used:
  • as a substrate to assay N-acetyl-β-D-glucosaminidase (NAG)[1]
  • as a substrate to study chitinase ChiB1 activity[2]
  • to assess degranulation using rat basophilic leukemia (RBL)-2H3 cells[3]

Biochem/physiol Actions

4-Nitrophenyl N-acetyl-β-D-glucosaminide (NP-GlcNAc) is a widely used hexosaminidase substrate. Enzymatic action cleaves the glycosidic bond and forms 4-nitrophenolate (pNP) which is measured at 405 nm.[4] NP-GlcNAc can also be used in combination with diethylaminoethyl-a-cyclodextrin (DEn-CD) for a rapid and accurate rate assay method for b-N-acetylglucosaminidase. The cyclodextrin derivative is used as an additive to ionize 4-nitrophenol to yellow-colored 4-nitrophenoxide at a pH near 5, the pH optimum for the enzyme.

Substrates

Chromogenic substrate for N-acetyl-glucosaminidase.

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
0000378541
0000378541
0000378542
0000341675
0000340336

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Chromogenic carbamate and acetal substrates for glycosaminidases
Chibba A, et al.
Carbohydrate Chemistry, 549-558 null
Femke Waanders et al.
American journal of kidney diseases : the official journal of the National Kidney Foundation, 53(1), 16-25 (2008-10-01)
Tubulointerstitial damage plays an important role in chronic kidney disease (CKD) with proteinuria. Urinary kidney injury molecule 1 (KIM-1) reflects tubular KIM-1 and is considered a sensitive biomarker for early tubular damage. We hypothesized that a decrease in proteinuria by
Yajun Zhou et al.
FEMS microbiology letters, 363(12) (2016-05-18)
We purified a chitinase from pilei extractions of Coprinopsis cinerea fruiting bodies by ammonium sulfate precipitation and CM Sepharose cation exchange chromatography. MALDI-TOF/TOF MS analysis characterized this purified chitinase as a putative class V chitinase, ChiB1. ChiB1 hydrolyzed colloidal chitin
Andrzej Temeriusz et al.
Carbohydrate research, 341(15), 2581-2590 (2006-09-05)
The X-ray diffraction analysis of N-o-nitrophenyl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylamine (1), N-m-nitrophenyl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylamines, N-p-nitrophenyl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylamines, and their N-acetyl derivatives was performed. The sugar moieties always adopt (4)C1 conformations, however, due to crystal packing forces they are always slightly distorted. It was found that except N-acetyl, N-m-nitrophenyl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylamine
K Masaki et al.
Journal of protein chemistry, 20(2), 107-113 (2001-09-21)
Bombyx mori lysozyme is 10 amino acids shorter than hen egg-white lysozyme, which is a typical c-type lysozyme. It was expressed by using the methylotrophic yeast Pichia pastoris. The thermal stability and the enzymatic activity of the Bombyx mori lysozyme
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