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M9763

Sigma-Aldrich

4-Methylumbelliferyl β-D-N,N′-diacetylchitobioside hydrate

fluorogenic, ≥98% (TLC), powder

Synonym(s):

4-Methylumbelliferyl-N,N′-diacetyl-β-D-chitobioside hydrate

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About This Item

Empirical Formula (Hill Notation):
C26H34N2O13 · xH2O
CAS Number:
Molecular Weight:
582.55 (anhydrous basis)
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.28

product name

4-Methylumbelliferyl β-D-N,N′-diacetylchitobioside hydrate, ≥98% (TLC)

Quality Level

Assay

≥98% (TLC)

form

powder

solubility

DMF: 9.80-10.20 mg/mL, clear, colorless to light yellow

fluorescence

λex 330 nm; λem 375 nm in methanol

storage temp.

−20°C

SMILES string

CC(=O)NC1C(O)C(O)C(CO)OC1OC2C(O)C(NC(C)=O)C(OC2CO)Oc3ccc4C(C)=CC(=O)Oc4c3

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)

InChI key

UPSFMJHZUCSEHU-UHFFFAOYSA-N

Application

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.

Biochem/physiol Actions

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 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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Genomic analysis and initial characterization of the chitinolytic system of Microbulbifer degradans strain 2-40
Howard MB, et al.
Journal of Bacteriology, 185(11), 3352-3360 (2003)
Human gastric juice contains chitinase that can degrade chitin
Paoletti MG, et al.
Annals of Nutrition & Metabolism, 51(3), 244-251 (2007)
Functional comparison of recombinant acidic mammalian chitinase with enzyme from murine bronchoalveolar lavage
Goedken ER, et al.
Protein Expression and Purification, 75(1), 55-62 (2011)
Quantification of Chitinase Activity in Fusarium oxysporum
Ruiz-Roldan C and Roncero MIG
Bio-protocol, 6(15) (2016)
Polysaccharidases in the crystalline styles of selectively bred Greenshell mussel (Perna canaliculus Gmelin) families
Mackenzie AL and Marshall C
Journal of shellfish research., 33(3), 687-694 (2014)

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