H-Thr-AMC is a threonine-based amino acid derivative featuring a free α-amino group (as the H-threonyl moiety) and a threonine side chain bearing a β-hydroxyl substituent, with the carboxyl functionality converted to an AMC (7-amino-4-methylcoumarin) amide. The molecule therefore contains the threonine amino acid framework while presenting a coumarin fluorophore (AMC) as the leaving-group/label element, enabling monitoring of substrate turnover through the coumarin chromophore rather than relying on the native amino acid carboxyl group. H-Thr-AMC is used in biochemical assay development and enzyme-substrate studies where threonine recognition is probed using an AMC-linked substrate analogue, and it can also serve as a labeled amino acid reagent for analytical method development involving fluorescence-based readouts.
CAT No: CP26587
CAS No:191723-66-7
Synonyms/Alias:L-Threonine7-amido-4-methylcoumarin;191723-66-7;CTK8E6831;Butanamide,2-amino-3-hydroxy-N-(4-methyl-2-oxo-2H-1-benzopyran-7-yl)-,(2S,3R)-;ZINC2517193;AKOS025294808;L-Threonine7-amido-4-methylcoumarin;VC31097;RT-013540
H-Thr-AMC is a threonine-based fluorogenic amide in which the amino acid is linked to 7-amino-4-methylcoumarin (AMC) through the side-chain carboxamide, yielding a chiral amino acid scaffold that presents a free hydroxyl group on the threonine side chain while maintaining an amide-linked coumarin chromophore. The molecule bears an N-terminal thioamide-like acyl linkage pattern consistent with peptide-derivative chemistry and a coumarin fluorophore whose emission is sensitive to cleavage or hydrolysis events that release AMC. The stereochemistry at the threonine center governs side-chain orientation and can influence substrate recognition by enzymes or binding proteins in chemical biology assays. As a compact amino acid derivative with a built-in reporting group, H-Thr-AMC functions as a biochemical research intermediate and analytical substrate precursor for downstream derivatization and method development.
1. Enzyme Activity Assays
H-Thr-AMC is applied in enzymology and chemical biology workflows where coumarin-based fluorogenic substrates enable real-time monitoring of protease, peptidase, or amidase activity. The threonine moiety provides a stereodefined amino acid recognition element with a side-chain hydroxyl that can participate in hydrogen-bonding interactions within enzyme active sites. The AMC reporting group is incorporated as an amide-linked leaving fragment, so enzymatic cleavage can generate a measurable fluorescence signal that supports kinetic profiling. Downstream use includes preparing assay panels for substrate specificity mapping and generating structurally related amino acid AMC derivatives for comparative enzyme characterization.
2. Peptidomimetic Substrate Design
H-Thr-AMC is utilized in peptidomimetic and molecular recognition studies where amino acid-coumarin conjugates serve as tractable substrate analogs for structure-function investigations. The defined threonine stereocenter and side-chain hydroxyl provide a chemically realistic motif for modeling how polar amino acid functionality is positioned in peptide-like binding pockets. The amide linkage to the AMC chromophore allows systematic variation of neighboring protecting-group patterns or side-chain modifications in synthetic campaigns aimed at tuning cleavage susceptibility. Resulting derivatives can be applied to SAR studies of enzyme substrate preferences and to the design of selective inhibitors or mechanistic probes through substrate analog libraries.
3. Analytical Research Standards
H-Thr-AMC is suitable for analytical research as a fluorogenic reference compound and calibration substrate in method development for coumarin-based detection systems. The stable amino acid-AMC conjugation provides a defined chemical entity with a characteristic fluorescence response upon cleavage, enabling assay normalization across experimental runs. The presence of the threonine hydroxyl and the amide-linked coumarin framework supports reproducible chromatographic and spectroscopic behavior when used as a standard for LC-fluorescence or fluorescence-based quantitation. Downstream utility includes creating internal standards for monitoring derivatization steps and for validating analytical workflows involving amino acid derivative substrates.
4. Protected Amino Acid Chemistry
H-Thr-AMC is employed as an amino acid derivative platform in synthetic organic chemistry where threonine-derived motifs can be adapted to protected amino acid synthesis strategies. The molecule's N-acylated amino acid framework and the side-chain hydroxyl enable planning of orthogonal protection and deprotection sequences when generating related threonine building blocks or coupling-ready intermediates. The AMC chromophore functions as a functional handle that can be retained or transformed depending on the desired downstream substrate or labeling format. Broader relevance includes supporting the preparation of coumarin-tagged amino acid intermediates for peptide coupling chemistry and for constructing fluorescent readouts attached to amino acid backbones.
5. Industrial Fine Chemical Synthesis
H-Thr-AMC can be integrated into industrial fine chemical synthesis as a fluorogenic amino acid derivative intermediate for producing enzyme assay reagents and specialty analytical substrates. The coumarin chromophore and threonine stereocenter impose defined structural specifications that align with controlled manufacturing of chiral amino acid derivatives and reporting-group conjugates. The amide linkage pattern enables scalable synthetic route design that can incorporate protecting-group management for the amino acid hydroxyl and for coupling compatibility with AMC installation. Downstream manufacturing use includes supplying reagent-grade substrate families for process monitoring in biochemical R&D settings and for generating consistent analytical tools used in industrial biocatalysis development.
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