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M9763

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

Name: 4-Methylumbelliferyl β-<SC>D</SC>-N,N′-diacetylchitobioside hydrate
Brand: SIGMA

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:

53643-12-2

Molecular Weight:

582.55 (anhydrous basis)

MDL number:

MFCD00082499

UNSPSC Code:

12352204

PubChem Substance ID:

24897364

NACRES:

NA.28

product name

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

Quality Level

200

Assay

≥98% (TLC)

form

powder

solubility

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

fluorescence

λ_ex 330 nm; λ_em 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.

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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Human gastric juice contains chitinase that can degrade chitin

Paoletti MG, et al.

Annals of Nutrition & Metabolism, 51(3), 244-251 (2007)

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)

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)

Tertiary interactions in the folding pathway of hen lysozyme: kinetic studies using fluorescent probes.

L S Itzhaki et al.

Biochemistry, 33(17), 5212-5220 (1994-05-03)

The refolding kinetics of hen lysozyme have been studied using a range of fluorescent probes. These experiments have provided new insight into the nature of intermediates detected in our recent hydrogen-exchange labeling studies [Radford, S.E., et al. (1992) Nature 358

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