Ac-Ala-Val-Ome presents an acetylated N-terminus and a methyl ester tail that streamline analysis of peptide stability and hydrolysis. Alanine and valine create a compact hydrophobic core that influences conformational behavior. The protected ester enhances studies of cleavage kinetics and enzymatic selectivity. Researchers apply this compound to peptide synthesis strategy testing and small-molecule conjugation design.
CAT No: R2428
CAS No:99141-91-0
Synonyms/Alias:ZZL-7;99141-91-0;Ac-Ala-Val-Ome;GTPL12316;GLXC-27170;DA-68896;MS-23459;HY-148417;CS-0624032;(S)-Methyl 2-((S)-2-acetamidopropanamido)-3-methylbutanoate;methyl (2S)-2-[(2S)-2-acetamidopropanamido]-3-methylbutanoate;
Ac-Ala-Val-Ome, also known as N-acetyl-alanyl-valine methyl ester, is a synthetic dipeptide derivative that serves as a valuable tool in peptide research and biochemical studies. This compound features an acetylated N-terminus and a methyl esterified C-terminus, which enhance its stability and modulate its physicochemical properties. With its compact peptide backbone, Ac-Ala-Val-Ome is particularly amenable to structural studies, enzymatic assays, and synthetic applications. Its defined sequence and terminal modifications make it a versatile building block for investigating peptide activity, stability, and interactions, offering researchers a reliable substrate for probing various aspects of peptide chemistry and biology.
Peptide Synthesis: Ac-Ala-Val-Ome is widely utilized as a protected dipeptide intermediate in solid-phase and solution-phase peptide synthesis. The acetyl and methyl ester groups safeguard the N- and C-termini, respectively, preventing undesired side reactions during chain elongation. Researchers often employ this compound to introduce specific dipeptide motifs into larger peptide chains, facilitating the assembly of custom sequences for structure-activity relationship studies or the creation of novel bioactive peptides. Its use streamlines the synthetic workflow, particularly when producing peptides with challenging sequences or when precise control over terminal modifications is required.
Enzyme Substrate Studies: As a model substrate, N-acetyl-alanyl-valine methyl ester enables detailed investigation of peptidase and protease specificity. Its defined structure allows scientists to assess enzyme cleavage preferences, kinetic parameters, and substrate recognition mechanisms. By incorporating this dipeptide into enzymatic assays, researchers can systematically evaluate how structural modifications influence enzymatic activity, providing insights into enzyme-substrate interactions and contributing to the design of selective inhibitors or probes for proteolytic enzymes.
Peptide Transport and Uptake Research: The methyl ester modification in Ac-Ala-Val-Ome enhances membrane permeability, making it a useful probe for studying peptide transport mechanisms across biological membranes. In cellular uptake experiments, this compound helps elucidate the roles of transporters and passive diffusion in peptide absorption. By tracking the cellular localization and intracellular processing of this dipeptide, scientists gain a deeper understanding of peptide pharmacokinetics, which can inform the design of more efficient peptide-based delivery systems or therapeutic agents.
Structural Biology and Conformational Analysis: The well-defined and relatively simple structure of N-acetyl-alanyl-valine methyl ester makes it an ideal candidate for conformational studies using spectroscopic techniques such as NMR or circular dichroism. Researchers leverage this compound to investigate the influence of terminal modifications on peptide backbone flexibility, secondary structure formation, and intramolecular interactions. Insights gained from these studies can be extrapolated to larger peptides and proteins, aiding in the rational design of stable peptide scaffolds or mimetics with desired structural properties.
Chemical Biology Tool Development: Ac-Ala-Val-Ome serves as a foundational element in the development of chemical probes and affinity tags for biological research. By incorporating this dipeptide into larger molecular constructs, scientists can create tools for labeling, tracking, or isolating specific biomolecules in complex mixtures. The stability and reactivity conferred by its terminal modifications enable selective conjugation strategies, expanding the repertoire of chemical biology techniques available for studying protein-protein interactions, post-translational modifications, or cellular signaling pathways.
Peptide-based Material Science: In addition to its roles in biochemical and biological research, N-acetyl-alanyl-valine methyl ester finds application in the field of peptide-based material science. Its structural features make it a valuable building block for the design of self-assembling peptide materials, nanostructures, or hydrogels. By manipulating the sequence and terminal groups, researchers can tailor the assembly behavior, mechanical properties, and functionalization potential of these materials. Such innovations have far-reaching implications for developing advanced biomaterials for tissue engineering, drug delivery, or biosensing applications. Through its multifaceted roles, Ac-Ala-Val-Ome continues to support progress across peptide science, enabling researchers to explore new frontiers in chemistry, biology, and materials research.
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