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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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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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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)
Quantification of Chitinase Activity in Fusarium oxysporum
Ruiz-Roldan C and Roncero MIG
Bio-protocol, 6(15) (2016)
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)
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)

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