122147-95-9

Usage

Uses

Used in Organic Synthesis:
4-Methylumbelliferyl β-D-chitobiose peracetate is used as a synthetic intermediate in the preparation of various complex carbohydrates, glycoconjugates, and bioactive molecules. Its unique structure and fluorescent properties make it a valuable building block for the development of new pharmaceuticals, diagnostics, and materials with potential applications in the life sciences.
Used in Enzyme Assays:
Due to the presence of the 4-methylumbelliferone group, 4-METHYLUMBELLIFERYL B-D-CHITOBIOSE PERACETATE can be used in enzyme assays to detect and quantify the activity of specific enzymes, such as chitinases and β-N-acetylglucosaminidases. Upon enzymatic cleavage, the 4-MU group is released, producing a fluorescent signal that can be easily measured, allowing for the sensitive and specific detection of enzyme activity.
Used in Research and Development:
4-Methylumbelliferyl β-D-chitobiose peracetate is employed as a research tool in the study of carbohydrate chemistry, glycobiology, and related fields. Its unique structure and properties make it a useful probe for investigating the structure-function relationships of carbohydrates and their interactions with proteins, lipids, and other biomolecules.
Used in Drug Discovery:
4-METHYLUMBELLIFERYL B-D-CHITOBIOSE PERACETATE may also be utilized in drug discovery efforts, particularly in the development of glycomimetics and other carbohydrate-based therapeutic agents. Its ability to serve as a synthetic intermediate and its fluorescent properties make it a promising candidate for the design and synthesis of novel drugs targeting carbohydrate-binding proteins and related pathways.

Upstream product

• 108-46-3 recorcinol 
• 72626-61-0 4-methylumbellifer-7-yl-β-D-cellobioside 
• 108-24-7 acetic anhydride 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 14227-66-8 acetobromocellobiose 

Downstream Products

• 72626-61-0 4-methylumbellifer-7-yl-β-D-cellobioside 

Relevant academic research and scientific papers

Rational design, synthesis, evaluation and enzyme - Substrate structures of improved fluorogenic substrates for family 6 glycoside hydrolases

Methylumbelliferyl-β-cellobioside (MUF-G2) is a convenient fluorogenic substrate for certain β-glycoside hydrolases (GH). However, hydrolysis of the aglycone is poor with GH family 6 enzymes (GH6), despite strong binding. Prediction of the orientation of the aglycone of MUF-G2 in the +1 subsite of Hypocrea jecorina Cel6A by automated docking suggested umbelliferyl modifications at C4 and C6 for improved recognition. Four modified umbelliferyl-β-cellobiosides [6-chloro-4-methyl- (ClMUF); 6-chloro-4-trifluoromethyl- (ClF3MUF); 4-phenyl- (PhUF); 6-chloro-4-phenyl- (ClPhUF)] were synthesized and tested with GH6, GH7, GH9, GH5 and GH45 cellulases. Indeed the rate of aglycone release by H. jecorina Cel6A was 10-150 times higher than with MUF-G2, although it was still three orders of magnitude lower than with H. jecorina Cel7B. The 4-phenyl substitution drastically reduced the fluorescence intensity of the free aglycone, while ClMUF-G2 could be used for determination of kcat and KM for H. jecorina Cel6A and Thermobifida fusca Cel6A. Crystal structures of H. jecorina Cel6A D221A mutant soaked with the MUF-, ClMUF- and ClPhUF-β-cellobioside substrates show that the modifications turned the umbelliferyl group 'upside down', with the glycosidic bond better positioned for protonation than with MUF-G2. 2012 The Authors Journal compilation

Glycosynthase-catalysed syntheses at pH below neutrality

The use of the new glycosynthase Ta-β-GlyE386G and of the already known Ss-β-GlyE387G for the synthesis of interesting 4-methylumbelliferyl disaccharides and for the galactosylation of α- and β-xylosides of 4-penten-1-ol is reported. The results show sati