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N9003

Sigma-Aldrich

4-Nitrophenyl N-acetyl-β-D-galactosaminide

≥98%

Synonym(s):

4-Nitrophenyl 2-acetamido-2-deoxy-β-D-galactopyranoside, p-Nitrophenyl N-acetyl-β-D-galactosaminide

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About This Item

Empirical Formula (Hill Notation):
C14H18N2O8
CAS Number:
Molecular Weight:
342.30
Beilstein:
96194
EC Number:
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.28

Assay

≥98%

form

powder

solubility

DMF: 50 mg/mL

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-RKQHYHRCSA-N

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General description

4-Nitrophenyl N-acetyl-β-D-galactosaminide is a chromogenic substrate for enzymes N-acetyl-β-D-galactosaminidase and N-Acetyl-β-D-hexosaminidase. It is membrane-permeable and serves as a substrate for the enzyme 6-sulfotransferase in Golgi vesicles.

Application

4-Nitrophenyl N-acetyl-β-D-galactosaminide has been used:
  • as a synthetic substrate in the glycosyl hydrolase assay of Yersinia pseudotuberculosis protein
  • as a substrate in -β-hexosaminidase assay in adenocarcinomic human alveolar basal epithelial cells A549
  • as a substrate for N-acetyl-β-D-galactosaminidase assay in rat kidney tissue extracts

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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Loss of a biofilm-inhibiting glycosyl hydrolase during the emergence of Yersinia pestis
Erickson DL, et al.
Journal of Bacteriology, 190(24), 8163-8170 (2008)
Lysosomal enzymes are decreased in the kidney of diabetic rats
Peres GB, et al.
Biochimica et Biophysica Acta (BBA)-Molecular Basis of Disease, 1832(1), 85-95 (2013)
Heterologous expression and characterization of an N-acetyl-beta-D-hexosaminidase from Lactococcus lactis ssp. lactis IL1403
Nguyen HA, et al.
Journal of Agricultural and Food Chemistry, 60(12), 3275-3281 (2012)
S K Chatterjee et al.
Cancer, 49(1), 128-135 (1982-01-01)
Levels and isoenzyme profiles of beta-hexosaminidase were compared in extracts from normal ovarian and ovarian epithelial tumors. The specific activities of beta-hexosaminidase were significantly (P less than 0.001) higher in malignant than in normal ovarian tissues. The enzyme levels of
R D Roer et al.
Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology, 128(4), 683-690 (2001-04-06)
We have previously demonstrated a marked change in sugar moieties of glycoproteins of the cuticle of the blue crab, Callinectes sapidus, between 0.5 and 3 h post-ecdysis. The present study has identified a glycosidase that appears in the cuticle during

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