D-Ala-Leu integrates a D-amino acid with a hydrophobic L-residue, offering a platform to study stereochemical effects on peptide stability. The sequence reveals altered backbone geometry that impacts folding and enzyme recognition. Researchers use it to evaluate chirality-driven binding properties. Applications span peptide engineering, conformational analysis, and synthetic method testing.
CAT No: R2422
CAS No:67113-60-4
Synonyms/Alias:D-Ala-Leu;67113-60-4;D-alanyl-L-leucine;L-Leucine, D-alanyl-;H-D-ALA-LEU-OH;(S)-2-((R)-2-Aminopropanamido)-4-methylpentanoic acid;(2S)-2-[(2R)-2-aminopropanamido]-4-methylpentanoic acid;D-alanylleucine;d-Alanyl-l-leucin;D-Ala-L-Leu;SCHEMBL7651656;CHEBI:73838;MFCD00066033;AKOS010842261;HY-W212029;BS-24800;CS-0274596;F87608;EN300-7374554;Q27144160;(S)-2-((R)-2-Aminopropanamido)-4-methylpentanoicacid;
D-Ala-Leu is a synthetic dipeptide composed of D-alanine and L-leucine, representing a valuable tool in the study of peptide structure, function, and enzymatic specificity. As a chiral peptide featuring both D- and L-amino acid residues, it offers unique opportunities for probing stereochemical influences in biochemical systems. Its distinct configuration makes it particularly relevant to research on proteolytic stability, peptide-mimetic design, and the investigation of peptide transport and metabolism. The compound's versatility and defined structure underpin its widespread adoption in peptide research, enzymology, and analytical biochemistry.
Peptide stability studies: Researchers frequently utilize D-Ala-Leu to examine the effects of D-amino acid incorporation on peptide stability against enzymatic degradation. The presence of a D-alanine residue at the N-terminus confers resistance to many common proteases, enabling detailed investigations into peptide half-life, degradation pathways, and the development of protease-resistant analogs. Such studies are critical for understanding peptide turnover in biological systems and for designing bioactive peptides with enhanced metabolic stability.
Enzyme specificity assays: The dipeptide serves as a model substrate in assays designed to elucidate the substrate preferences and catalytic mechanisms of peptidases and proteases. By comparing the hydrolysis rates of peptides containing D- versus L-amino acids, scientists can dissect the stereochemical requirements of various enzymes. This approach aids in characterizing enzyme selectivity, mapping active site architecture, and screening for inhibitors or modulators relevant to both basic research and industrial biocatalysis.
Peptide transport investigations: D-Ala-Leu is employed in studies of peptide transport systems, particularly those involved in the uptake of di- and oligopeptides across cell membranes. Its mixed chirality allows researchers to distinguish between transporter subtypes that recognize D-containing peptides versus those selective for all-L sequences. Such research contributes to a deeper understanding of nutrient absorption, drug delivery mechanisms, and the molecular basis of transporter specificity in prokaryotic and eukaryotic systems.
Analytical method development: The dipeptide is often used as a standard or calibration compound in chromatographic and mass spectrometric methods for peptide analysis. Its defined structure and distinct chromatographic behavior facilitate the optimization of separation protocols, the validation of detection sensitivity, and the assessment of instrument performance. This application supports high-precision analytical workflows in quality control, peptide synthesis monitoring, and biochemical research.
Peptide-mimetic design: Incorporation of D-Ala-Leu motifs into larger peptide sequences is a strategy employed in the development of peptide-mimetics and peptidomimetics with tailored biological properties. The altered backbone conformation induced by the D-residue can modulate receptor binding, reduce immunogenicity, and enhance resistance to enzymatic breakdown. This approach is integral to the rational design of novel research probes, biochemical tools, and functionalized biomolecules for diverse experimental applications.
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