D-Leucylglycylglycine combines a D-configured hydrophobic residue with two flexible glycines, enabling stereochemical and conformational analysis. The sequence helps dissect how D-residues alter backbone geometry and recognition by proteases. Researchers evaluate its folding behavior and stability in solution. Applications include chirality studies, peptidomimetic design, and enzyme-specificity profiling.
CAT No: R2369
CAS No:18625-22-4
Synonyms/Alias:18625-22-4;D-Leucylglycylglycine;(R)-2-(2-(2-Amino-4-methylpentanamido)acetamido)acetic acid;2-[[2-[[(2R)-2-amino-4-methylpentanoyl]amino]acetyl]amino]acetic acid;CHEMBL1222388;H-D-Leu-Gly-Gly-OH;2-[[2-[[(2R)-2-azaniumyl-4-methylpentanoyl]amino]acetyl]amino]acetate;D-Leucyl-glycyl-glycine;Glycine,D-leucylglycyl-;Glycine, N-(N-D-leucylglycyl)-;N-(N-D-Leucylglycyl)glycine;2-{2-[(2R)-2-Amino-4-methylpentanamido]acetamido}acetic acid;EINECS 242-457-0;D-LEU-GLY-GLY;(([(2-Amino-4-methylpentanoyl)amino]acetyl)amino)acetic acid #;{2-[(2R)-2-amino-4-methylpentanamido]acetamido}acetic acid;DTXSID601314917;(R)-2-(2-(2-Amino-4-methylpentanamido)-acetamido)acetic acid;TAA62522;BDBM50410267;AKOS015854090;NSC 523307;AS-70790;CS-0320767;L0031;NS00085542;A12180;(R)-2-(2-(2-Amino-4-methylpentanamido)acetamido)aceticacid;
D-Leucylglycylglycine is a synthetic tripeptide composed of D-leucine, glycine, and glycine residues, notable for its unique stereochemistry and modular peptide structure. As a versatile carbohydrate compound analog, it serves as a valuable tool in biochemical research, peptide engineering, and enzymology. The incorporation of a D-amino acid at the N-terminus distinguishes this tripeptide from its all-L counterparts, imparting increased resistance to proteolytic degradation and altering its interaction profile with various biological molecules. Its defined sequence and chirality make it an ideal candidate for investigating peptide stability, substrate specificity, and the influence of stereochemistry on peptide function. Researchers leverage D-Leucylglycylglycine for a range of experimental applications, utilizing its physicochemical properties to advance the understanding of peptide-based systems and molecular recognition processes.
Peptide Transport Studies: D-Leucylglycylglycine is frequently employed in the study of peptide transport mechanisms, particularly within cellular and membrane models. By using this tripeptide as a substrate, scientists can examine the selectivity and efficiency of peptide transporters, such as those in the SLC15 family, which are responsible for the uptake of small peptides across biological membranes. The inclusion of the D-leucine residue enables the differentiation between transporter affinities for D- versus L-configured peptides, aiding in the elucidation of transporter specificity and function. This research is critical for understanding nutrient absorption, drug delivery, and the physiological regulation of peptide transport.
Enzyme Substrate Specificity: As a substrate analog, D-Leucylglycylglycine provides insight into the substrate specificity of various peptidases and proteases. Its resistance to rapid enzymatic hydrolysis due to the D-amino acid substitution allows researchers to probe enzyme active sites and determine the structural requirements for catalysis. By comparing the hydrolysis rates of this compound with those of all-L tripeptides, investigators can map out the stereochemical preferences of enzymes and identify potential inhibitors or modulators. Such studies contribute to the design of more stable peptide-based drugs and inhibitors for therapeutic or research purposes.
Peptide Stability and Metabolism: The presence of a D-amino acid at the N-terminus of D-Leucylglycylglycine confers enhanced stability against exopeptidase-mediated degradation. This property is exploited in metabolic studies where researchers seek to understand the fate of peptides in biological fluids or tissue extracts. By tracking the degradation profile of this tripeptide, scientists can assess the impact of stereochemistry on peptide half-life and identify metabolic pathways that selectively process D-containing peptides. These findings have implications for the development of peptide therapeutics with improved in vivo stability.
Structure-Activity Relationship Analysis: In structure-activity relationship (SAR) studies, D-Leucylglycylglycine serves as a model compound to dissect the influence of amino acid configuration on biological activity. Modifying the peptide backbone with a D-amino acid allows researchers to systematically evaluate how changes in stereochemistry affect receptor binding, signaling, or biological recognition events. This approach facilitates the rational design of bioactive peptides with tailored properties, enabling the optimization of lead compounds for research or biotechnological applications.
Analytical Method Development: Analytical chemists utilize D-Leucylglycylglycine as a standard or reference compound in the development and validation of chromatographic and spectrometric methods for peptide analysis. Its defined structure and unique stereochemistry make it an excellent candidate for testing the resolution and sensitivity of analytical techniques such as HPLC, LC-MS, or capillary electrophoresis. By incorporating this tripeptide into method development workflows, laboratories can ensure accurate quantification and identification of peptide analytes in complex mixtures.
Biomolecular Interaction Studies: D-Leucylglycylglycine is also applied in studies of biomolecular interactions, including investigations of peptide-receptor binding, protein-peptide docking, or antibody recognition. Its resistance to proteolytic cleavage and altered conformational preferences due to the D-leucine residue allow researchers to explore non-canonical peptide binding modes and develop stable peptide probes for affinity assays or structural biology experiments. Through these diverse applications, D-Leucylglycylglycine continues to support innovative research in peptide science, molecular biology, and analytical chemistry, driving advancements in our understanding of peptide behavior and function.
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