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 is a synthetic peptide derivative characterized by an N-terminal acetyl group, a dipeptide backbone of alanine and valine, and a C-terminal methyl ester modification. This compound exemplifies a class of protected peptide fragments frequently utilized in peptide chemistry and biochemical research. Its structural features, including the acetylated N-terminus and methyl ester-protected C-terminus, confer both stability and versatility, making it a valuable intermediate for peptide synthesis and functional studies. The presence of non-polar amino acid residues further enhances its relevance in investigations of peptide conformation, hydrophobic interactions, and sequence-specific effects in protein engineering and enzymology.
Peptide Synthesis: As a protected dipeptide building block, Ac-Ala-Val-Ome is widely employed in solid-phase and solution-phase peptide synthesis protocols. The acetyl and methyl ester groups safeguard reactive termini, enabling selective elongation of peptide chains without undesired side reactions. Researchers utilize this compound to streamline the assembly of longer oligopeptides or to introduce specific sequence motifs at defined positions within custom peptides. Its use supports high-fidelity synthesis workflows, facilitating the generation of peptides for structural, functional, or mechanistic studies.
Enzyme Substrate Design: The structural configuration of Ac-Ala-Val-Ome makes it a valuable substrate or intermediate in the development of enzyme assays, particularly those targeting proteases or peptidases. By incorporating this dipeptide fragment into model substrates, scientists can probe enzyme specificity, cleavage mechanisms, and substrate preferences. The methyl ester group at the C-terminus can be exploited to modulate enzyme recognition or to generate prodrugs and masked substrates for kinetic analysis, providing insights into enzyme-substrate interactions at the molecular level.
Peptide Modification Studies: The acetylated and methyl-esterified termini of this compound offer a platform for systematic studies of peptide modifications. Researchers leverage Ac-Ala-Val-Ome to investigate the effects of terminal protection on peptide stability, solubility, and resistance to enzymatic degradation. These studies are critical for optimizing peptide-based reagents, designing stable biomaterials, and understanding the influence of chemical modifications on peptide behavior in biological and analytical contexts.
Hydrophobicity and Structure-Activity Relationship (SAR) Research: The presence of alanine and valine, both hydrophobic amino acids, renders this dipeptide fragment particularly suitable for exploring the role of side-chain hydrophobicity in peptide folding, aggregation, and biological activity. By incorporating Ac-Ala-Val-Ome into peptide libraries or model systems, scientists can dissect the contributions of specific sequence motifs to secondary structure formation, molecular recognition, and intermolecular interactions. Such investigations are essential for rational peptide design and for elucidating fundamental principles of protein chemistry.
Analytical Method Development: The defined structure and chemical stability of Ac-Ala-Val-Ome make it an excellent reference compound or standard in analytical method development. It is frequently used to calibrate chromatographic systems, validate mass spectrometric detection protocols, and optimize sample preparation techniques for peptide analysis. Employing this dipeptide as a standard aids in ensuring reproducibility and accuracy in quantitative and qualitative analyses of peptides and related biomolecules across research and industrial laboratories.
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