4-Methylumbelliferyl β-D-N,N'-diacetylchitobioside - ≥98% , CAS No.53643-12-2

CAS: 53643-12-2 Cat. No.: M769945 Molecular Weight: 582.55 (anhydrous basis)

GRADE & PURITY ≥98%

Synonyms

4-Methylumbelliferyl β-D-N,N′diacetylchitobioside hydrate | 7-[[2-(acetylamino)-4-O-[2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]-2-deoxy-β-D-glucopyranosyl]oxy]-4-methyl-2H-1-benzopyran-2-one

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

4-Methylumbelliferyl β-D-N,N′-diacetylchitobioside hydrate has been used as a fluorogenic substrate:
in chitinase enzyme assay of bronchoalveolar lavage samples；
in acidic mammalian chitinase activity assay of human gastric juice；
in chitinase assay in crystalline style extracts of Greenshell Mussels and fungus Fusarium oxysporum.

Specifications

Synonyms

4-Methylumbelliferyl β-D-N, N′diacetylchitobioside hydrate | 7-[[2-(acetylamino)-4-O-[2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]-2-deoxy-β-D-glucopyranosyl]oxy]-4-methyl-2H-1-benzopyran-2-one

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

4-Methylumbelliferyl β-D-N, N′-diacetylchitobioside hydrate (MUF-diNAG) is an analog of chitin. It is a fluorogenic substrate for chitin depolymerase and its breakdown results in methylumbelliferone, a fluorescent product.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

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

Purity

≥98%

Names and Identifiers

• Canonical Smiles: O=C(C)N[C@H]1[C@H](OC2=CC=C(C(C)=CC(O3)=O)C3=C2)O[C@H](CO)[C@@H](O[C@]4([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4NC(C)=O)[C@@H]1O
• IUPAC Name: N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6S)-5-acetamido-4-hydroxy-2-(hydroxymethyl)-6-(4-methyl-2-oxochromen-7-yl)oxyoxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• InChIKey: UPSFMJHZUCSEHU-JYGUBCOQSA-N
• INCHI: 1S/C26H34N2O13/c1-10-6-18(33)38-15-7-13(4-5-14(10)15)37-25-20(28-12(3)32)23(36)24(17(9-30)40-25)41-26-19(27-11(2)31)22(35)21(34)16(8-29)39-26/h4-7,16-17,19-26,29-30,34-36H,8-9H2,1-3H3,(H,27,31)(H,28,32)/t16-,17-,19-,20-,21-,22-,23-,24-,25-,26+/m1/s1
• Isomeric SMILES: CC1=CC(=O)OC2=C1C=CC(=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)NC(=O)C)O)NC(=O)C
• Molecular Weight: 582.55 (anhydrous basis)

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Coumarins and derivatives
      • Subclass Coumarin glycosides

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Coumarins and derivatives
• Subclass: Coumarin glycosides
• Intermediate Tree Nodes: Not available
• Direct Parent: Coumarin glycosides
• Alternative Parents: N-acyl-alpha-hexosamines Disaccharides O-glycosyl compounds 1-benzopyrans Pyranones and derivatives Oxanes Benzenoids Acetamides Heteroaromatic compounds Secondary alcohols Secondary carboxylic acid amides Lactones Oxacyclic compounds Acetals Hydrocarbon derivatives Carbonyl compounds Organic oxides Organonitrogen compounds Organopnictogen compounds Primary alcohols
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Coumarin-7-o-glycoside - Coumarin o-glycoside - N-acyl-alpha-hexosamine - Disaccharide - Glycosyl compound - O-glycosyl compound - Benzopyran - 1-benzopyran - Pyranone - Oxane - Pyran - Benzenoid - Acetamide - Heteroaromatic compound - Secondary alcohol - Secondary carboxylic acid amide - Carboxamide group - Lactone - Organoheterocyclic compound - Acetal - Carboxylic acid derivative - Oxacycle - Alcohol - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organonitrogen compound - Organooxygen compound - Carbonyl group - Organic nitrogen compound - Primary alcohol - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety.
• External Descriptors: Not available

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: 9.80-10.20 mg/mL, clear, colorless to light yellow
• Molecular Weight: 582.600 g/mol
• XLogP3: -2.900
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 8
• Exact Mass: 582.206 Da
• Monoisotopic Mass: 582.206 Da
• Topological Polar Surface Area: 223.000 Ų
• Heavy Atom Count: 41
• Formal Charge: 0
• Complexity: 994.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 10
• 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