Ala-His pairs a small aliphatic residue with an imidazole-bearing histidine, enabling investigation of proton-exchange mechanisms. The dipeptide supports studies of hydrogen bonding, pH-responsive interactions, and conformational sampling. Researchers employ it as a model for enzymatic recognition. Uses include peptide design, folding analysis, and biophysical characterization.
CAT No: R2460
CAS No:3253-17-6
Synonyms/Alias:Ala-His;H-Ala-His-OH;3253-17-6;L-alanyl-L-histidine;alanyl-histidine;Alanylhistidine;L-Ala-L-His;N-L-Alanyl-L-histidine;CHEMBL1221620;CHEBI:73771;DTXSID201016440;(S)-2-((S)-2-Aminopropanamido)-3-(1H-imidazol-5-yl)propanoic acid;(2S)-2-[[(2S)-2-aminopropanoyl]amino]-3-(1H-imidazol-5-yl)propanoic acid;CHEBI:74388;AH dipeptide;A-H Dipeptide;MFCD00037853;Alanine Histidine dipeptide;Alanine-Histidine dipeptide;SCHEMBL308989;XZWXFWBHYRFLEF-FSPLSTOPSA-N;DTXCID101474629;BDBM50348857;AKOS010421081;AKOS015893950;FA107964;NS00045703;F76020;Q27144099;(S)-2-((S)-2-Aminopropanamido)-3-(1H-imidazol-5-yl)propanoicacid;(S)-2-((S)-2-aminopropanamido)-3-(1H-imidazol-4-yl)propanoic acid;221-845-3;
Ala-His, also known as alanyl-histidine, is a dipeptide composed of the amino acids alanine and histidine linked by a single peptide bond. As a small peptide, it serves as an important biochemical tool in the study of peptide structure, function, and metabolism. Its unique combination of a nonpolar aliphatic residue (alanine) and an imidazole-containing, polar residue (histidine) imparts distinct physicochemical properties, making it valuable for probing peptide behavior in various biological and chemical contexts. Researchers utilize this dipeptide in diverse experimental systems to investigate fundamental aspects of peptide chemistry, enzymatic hydrolysis, and transport mechanisms, all of which contribute to a deeper understanding of peptide-related processes in biological systems.
Peptide transport studies: Ala-His is widely employed as a model substrate for investigating peptide transport systems, particularly the peptide transporter families such as PEPT1 and PEPT2. By tracking the uptake and translocation of this dipeptide across cellular membranes, researchers can elucidate the specificity, kinetics, and regulatory mechanisms governing peptide transport in epithelial and other cell types. These studies provide critical insights into nutrient absorption, drug delivery strategies, and the physiological roles of peptide carriers in health and disease.
Enzymatic hydrolysis research: As a defined dipeptide, alanyl-histidine serves as an ideal substrate for characterizing the activity of various peptidases and proteases. Enzyme assays utilizing this compound enable the assessment of substrate specificity, catalytic efficiency, and inhibition profiles of enzymes involved in peptide bond cleavage. Such experiments are essential for understanding proteolytic pathways, optimizing enzyme formulations, and designing inhibitors for both basic research and industrial biocatalysis applications.
Peptide structure-function analysis: The combination of alanine and histidine residues in Ala-His provides an excellent system for exploring the influence of side-chain properties on peptide conformation, stability, and reactivity. Researchers use this dipeptide to study hydrogen bonding, metal ion coordination, and the impact of pH on peptide behavior, leveraging the unique chemical environment provided by the histidine imidazole group. These analyses inform the design of novel peptides with tailored properties for research, diagnostic, or material science applications.
Analytical method development: Ala-His is frequently utilized as a reference standard or calibration compound in analytical techniques such as high-performance liquid chromatography (HPLC), capillary electrophoresis, and mass spectrometry. Its well-defined structure and chromatographic behavior facilitate the optimization and validation of analytical protocols for peptide detection, quantification, and characterization. This utility supports both routine laboratory workflows and the development of new analytical methodologies for peptide research.
Peptide synthesis optimization: In peptide chemistry, alanyl-histidine is often used as a model compound to evaluate and refine synthetic strategies, including solid-phase and solution-phase peptide synthesis. Its synthesis and purification provide valuable benchmarks for assessing coupling efficiency, protecting group strategies, and purification protocols. These studies contribute to the advancement of peptide synthesis technologies and support the reliable production of more complex peptide sequences for research and industrial purposes.
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