4-Methylumbelliferyl 6-thio-Palmitate-β-D-Glucopyranoside

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4-Methylumbelliferyl 6-thio-Palmitate-β-D-Glucopyranoside

4-Methylumbelliferyl 6-thio-Palmitate-β-D-Glucopyranoside | 229644-17-1

Catalog Number A18-0100
Category Fluorescent Enzyme Substrates
Molecular Formula C32H48O8S
Molecular Weight 592.78
Catalog Number Size Price Quantity
A18-0100 -- $--

Product Introduction

4-Methylumbelliferyl 6-thio-palmitate-β-D-glucopyranoside is a fluorogenic substrate for palmitoyl-protein thioesterase (PPT), a lysosomal hydrolase that removes long-chain fatty acyl groups from modified cysteine residues in proteins. It is cleaved by PPT to produce fluorescent moiety 4-MU. It can be used in the diagnosis of infantile neuronal ceroid lipofuscinosis (INCL).

Chemical Information

Synonyms Mu-6S-Palm-β-Glc; 4-methyl-7-[[6-S-(1-oxohexadecyl)-6-thio-β-D-glucopyranosyl]oxy]-2H-1-benzopyran-2-one
Purity ≥95%
IUPAC Name S-[[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-methyl-2-oxochromen-7-yl)oxyoxan-2-yl]methyl] hexadecanethioate
Canonical SMILES CCCCCCCCCCCCCCCC(=O)SCC1C(C(C(C(O1)OC2=CC3=C(C=C2)C(=CC(=O)O3)C)O)O)O
InChI InChI=1S/C32H48O8S/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-28(34)41-21-26-29(35)30(36)31(37)32(40-26)38-23-17-18-24-22(2)19-27(33)39-25(24)20-23/h17-20,26,29-32,35-37H,3-16,21H2,1-2H3/t26?,29-,30+,31-,32-/m1/s1
InChI Key XCNUAQFXJPMZLU-BPXMXZQQSA-N
Appearance White to Off-white Solid
Melting Point 123-125°C
  • Product Specification
  • Application
Storage Store at -20°C

4-Methylumbelliferyl 6-thio-Palmitate-β-D-Glucopyranoside, a fluorogenic substrate utilized in various biochemical and diagnostic settings, exhibits diverse applications. Here are four key applications:

Enzyme Activity Assays: Serving as a substrate for measuring β-D-glucosidase enzyme activity, this compound undergoes enzymatic cleavage, resulting in the release of the fluorescent product 4-methylumbelliferone. This product can be quantified with ease using fluorescence spectroscopy, providing researchers with a sensitive tool to monitor enzyme kinetics and screen for enzyme inhibitors or activators. The ability to precisely track enzymatic reactions aids in unraveling enzyme functionality and modulation within biological systems.

Lysosomal Storage Disorder Diagnostics: Utilized in diagnostic assays for lysosomal storage disorders like Gaucher and Fabry diseases, 4-Methylumbelliferyl 6-thio-Palmitate-β-D-Glucopyranoside enables clinicians to diagnose these genetic conditions promptly and accurately by measuring enzymatic activity in patient samples. Early and precise diagnosis is crucial for facilitating timely interventions and effective disease management, highlighting the significance of this substrate in clinical diagnostics.

Biochemical Research: An invaluable tool for studying glycosylation processes, this substrate plays a pivotal role in exploring the function and regulation of β-D-glucosidase enzymes. Researchers leverage its properties to investigate how changes in these enzymes impact cellular metabolism and disease states. The reliable fluorescence-based detection method empowers scientists to meticulously track enzyme activities within intricate biological samples, shedding light on the intricacies of enzyme modulation and cellular pathways.

High-Throughput Screening: Employed in high-throughput screening platforms for drug discovery, 4-Methylumbelliferyl 6-thio-Palmitate-β-D-Glucopyranoside facilitates the identification of potential therapeutic compounds that modulate enzyme activity. The substrate’s fluorogenic nature enables rapid and automated detection of positive hits, expediting the process of discovering novel drug candidates for diseases involving β-D-glucosidase enzymes. This streamlined approach accelerates the search for promising therapeutic agents, driving advancements in pharmacological research and drug development.

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