A fluorogenic substrate for chitinases and chitotriosidases
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4-Methylumbelliferyl-β-D-N,N',N''-Triacetylchitotrioside

Item No. 19715

Technical Information
Formal Name
7-[[O-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1→4)-O-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1→4)-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]oxy]-4-methyl-2H-1-benzopyran-2-one
CAS Number
53643-13-3
Synonyms
  • MUF-triNAG
Molecular Formula
C34H47N3O18
Formula Weight
Purity
≥98%
A crystalline solid
DMF: 5 mg/mlDMF: 5 mg/mlDMSO: 10 mg/mlDMSO: 10 mg/ml
λmax
317 nm
SMILES
CC(N[C@H]([C@H]1O)[C@H](OC2=CC=C(C(C)=CC(O3)=O)C3=C2)O[C@H](CO)[C@H]1O[C@@](O[C@@H]4CO)([H])[C@H](NC(C)=O)[C@@H](O)[C@@H]4O[C@]5([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5NC(C)=O)=O
InChi Code
InChI=1S/C34H47N3O18/c1-12-7-22(44)50-18-8-16(5-6-17(12)18)49-32-24(36-14(3)42)28(47)30(20(10-39)52-32)55-34-25(37-15(4)43)29(48)31(21(11-40)53-34)54-33-23(35-13(2)41)27(46)26(45)19(9-38)51-33/h5-8,19-21,23-34,38-40,45-48H,9-11H2,1-4H3,(H,35,41)(H,36
InChi Key
BNYGKUQXGBVTRE-JFWBNMEYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    4-Methylumbelliferyl-β-D-N,N',N''-triacetylchitotrioside is a fluorogenic substrate for chitinases and chitotriosidases.1,2,3 4-Methylumbelliferyl-β-D-N,N',N''-triacetylchitotrioside is cleaved by chitinases and chitotriosidases to release the fluorescent moiety 4-methylumbelliferyl (4-MU). 4-MU fluorescence is pH-dependent with excitation maxima of 320 and 360 nm at low (1.97-6.72) and high (7.12-10.3) pH, respectively, and an emission maximum ranging from 445 to 455 nM, increasing as pH decreases.4 It has been used to screen plasma samples for reduced chitotriosidase activity that may be indicative of lysosomal storage disorders.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Elmonem, M.A., Ramadan, D.I., Issac, M.S., et alBlood spot versus plasma chitotriosidase: A systematic clinical comparison. Clin. Biochem. 47(1-2), 38-43 (2014).

    2. Howard, M.B., Ekborg, N.A., Taylor, L.E., et alGenomic analysis and initial characterization of the chitinolytic system of Microbulbifer degradans strain 2-40. J. Bacteriol. 185(11), 3352-3360 (2003).

    3. Mukamolova, G.V., Murzin, A.G., Salina, E.G., et alMuralytic activity of Micrococcus luteus Rpf and its relationship to physiological activity in promoting bacterial growth and resuscitation. Mol. Microbiol. 59(1), 84-98 (2006).

    4. Zhi, H., Wang, J., Wang, S., et alFluorescent properties of hymecromone and fluorimetric analysis of hymecromone in compound dantong capsule. J. Spectrosc. 147128 (2013).