4-Nitrophenyl N-acetyl-β-D-galactosaminide - ≥98% , CAS No.14948-96-0

CAS: 14948-96-0 Cat. No.: N111844 Molecular Weight: 342.3 Beilstein Registry Number: 96194 EC Number: 239-024-3

GRADE & PURITY ≥98%

Synonyms

4-nitrophenyl N-acetyl-beta-D-galactosaminide | N-((2S,3R,4R,5R,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)tetrahydro-2H-pyran-3-yl)acetamide | 4-Nitrophenyl 2-acetamido-2-deoxy-β-D-galactopyranoside | p-Nitrophenyl N-acetyl-β-D-galactosaminide

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

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.

Specifications

Synonyms

4-nitrophenyl N-acetyl-beta-D-galactosaminide | N-((2S, 3R, 4R, 5R, 6R)-4, 5-Dihydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)tetrahydro-2H-pyran-3-yl)acetamide | 4-Nitrophenyl 2-acetamido-2-deoxy-β-D-galactopyranoside | p-Nitrophenyl N-acetyl-β-D-galactosaminide

Specifications & Purity

≥98%

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488186275
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488186275
• Canonical Smiles: CC(=O)NC1C(C(C(OC1OC2=CC=C(C=C2)[N+](=O)[O-])CO)O)O
• IUPAC Name: N-[(2S,3R,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)oxan-3-yl]acetamide
• InChIKey: OMRLTNCLYHKQCK-RKQHYHRCSA-N
• 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
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@H]([C@H](O[C@H]1OC2=CC=C(C=C2)[N+](=O)[O-])CO)O)O
• WGK Germany: 3
• Molecular Weight: 342.3
• Beilstein: 96194
• Reaxy-Rn: 25358208
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25358208&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Aminosaccharides
          • Level6 N-acyl-alpha-hexosamines

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Aminosaccharides
• Direct Parent: N-acyl-alpha-hexosamines
• Alternative Parents: Hexoses O-glycosyl compounds Nitrobenzenes Nitroaromatic compounds Phenoxy compounds Phenol ethers Oxanes Secondary alcohols Organic oxoazanium compounds Acetals Propargyl-type 1,3-dipolar organic compounds Carboximidic acids Oxacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic zwitterions Organic oxides Primary alcohols Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: N-acyl-alpha-hexosamine - Hexose monosaccharide - Glycosyl compound - O-glycosyl compound - Nitrobenzene - Phenoxy compound - Nitroaromatic compound - Phenol ether - Monocyclic benzene moiety - Monosaccharide - Oxane - Benzenoid - C-nitro compound - Organic nitro compound - Secondary alcohol - Organoheterocyclic compound - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Allyl-type 1,3-dipolar organic compound - Carboximidic acid - Carboximidic acid derivative - Acetal - Oxacycle - Organic oxoazanium - Organic oxide - Organic nitrogen compound - Hydrocarbon derivative - Organopnictogen compound - Alcohol - Organonitrogen compound - Organic zwitterion - Primary alcohol - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.
• External Descriptors: N-acetyl-beta-D-galactosaminide

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: DMF: 50 mg/mL
• Sensitivity: Heat sensitive；Moisture sensitive
• Melt Point(°C): 207°C
• Molecular Weight: 342.300 g/mol
• XLogP3: -0.400
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 342.106 Da
• Monoisotopic Mass: 342.106 Da
• Topological Polar Surface Area: 154.000 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 449.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Jing Li, Kunpeng Gao, Francesco Secundo, Xiangzhao Mao.  (2021)  Biochemical characterization of two β-N-acetylglucosaminidases from Streptomyces violascens for efficient production of N-acetyl-d-glucosamine.  FOOD CHEMISTRY,      [PMID:34167004] [10.1016/j.foodchem.2021.130393]