D-Ala-Lys-AMCA hydrochloride is a fluorescent dipeptide featuring a D-alanine residue and an AMCA label for monitoring enzymatic cleavage. The charged lysine side chain enhances solubility and interaction with catalytic pockets. Researchers use it in kinetic studies and mapping substrate specificity. Its hydrochloride form provides stable aqueous behavior.
CAT No: R2203
CAS No:2703746-41-0
Synonyms/Alias:D-Ala-Lys-AMCA hydrochloride;D-Ala-Lys-AMCA (hydrochloride);2703746-41-0;(2S)-6-[[2-(7-amino-4-methyl-2-oxochromen-3-yl)acetyl]amino]-2-[[(2R)-2-aminopropanoyl]amino]hexanoic acid;hydrochloride;AKOS040744053;HY-111956B;N2-(D-Alanyl)-N6-(2-(7-amino-4-methyl-2-oxo-2H-chromen-3-yl)acetyl)-L-lysine hydrochloride;MS-28667;PD126278;CS-0107380;G17093;
D-Ala-Lys-AMCA hydrochloride is a synthetic peptide conjugate featuring a D-alanine and lysine dipeptide backbone covalently linked to the 7-amino-4-methylcoumarin-3-acetic acid (AMCA) fluorophore, provided as a hydrochloride salt for enhanced solubility and stability. This compound is widely recognized for its utility in fluorescence-based biochemical assays, leveraging the spectral properties of AMCA to enable sensitive detection and quantification of peptide substrates in complex biological samples. Its unique structure, combining a peptide motif with a robust fluorescent tag, makes it especially valuable for applications in enzymology, protease research, and advanced bioanalytical techniques. The integration of a D-amino acid confers increased resistance to proteolytic degradation, thereby extending the functional lifetime of the probe in experimental systems and improving assay reliability.
Fluorescent substrate for protease assays: D-Ala-Lys-AMCA hydrochloride serves as a highly effective fluorogenic substrate in the study of protease activity, particularly for enzymes that recognize and cleave at D-alanine or lysine residues. Upon enzymatic cleavage of the peptide bond, the AMCA moiety is released, resulting in a measurable fluorescence signal that directly correlates with protease activity. This property enables precise kinetic analyses, substrate specificity profiling, and high-throughput screening of protease modulators in a variety of research settings, including drug discovery and enzymology.
Enzyme kinetics and mechanism studies: The compound is frequently employed in investigations of enzyme kinetics, offering a convenient and sensitive means to monitor reaction progress in real time. By tracking the increase in fluorescence as the peptide is hydrolyzed, researchers can determine key kinetic parameters such as Km and Vmax with high accuracy. The use of a D-amino acid at the N-terminus also allows for exploration of enzyme stereospecificity, providing valuable insights into the mechanistic preferences of different proteolytic enzymes.
Peptide transport and uptake research: D-Ala-Lys-AMCA hydrochloride is utilized in studies of peptide transport mechanisms across biological membranes, including investigations of peptide transporter specificity and substrate recognition. The fluorescent tag enables direct visualization and quantification of dipeptide uptake in cellular systems, facilitating the characterization of transporter function, inhibitor screening, and the elucidation of transport kinetics under various experimental conditions.
Fluorescence microscopy and imaging applications: The AMCA label incorporated within the peptide structure allows for its use in advanced fluorescence microscopy protocols. Researchers can employ this compound to monitor the localization, trafficking, and intracellular processing of peptide substrates in live or fixed cells. The distinct blue emission of AMCA provides spectral separation from other commonly used fluorophores, supporting multiplexed imaging strategies and enabling detailed spatial and temporal resolution of peptide dynamics in complex biological environments.
Assay development and optimization: D-Ala-Lys-AMCA hydrochloride is instrumental in the development and optimization of novel bioanalytical assays, including fluorescence-based detection platforms and microplate-based screening systems. Its stable fluorescence, coupled with the specificity of peptide-enzyme interactions, supports the creation of robust, reproducible assays for diverse applications such as inhibitor screening, enzyme activity profiling, and high-content analysis. The compound's chemical stability and compatibility with a variety of assay formats make it a versatile tool for method development in both academic and industrial research laboratories.
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