His-[D-2-ME-Trp]-Ala is a fragment of the growth hormone hexarelin.
CAT No: R1423
His-[D-2-ME-Trp]-Ala is a synthetic peptide comprising histidine, D-2-methyltryptophan, and alanine residues arranged in a defined sequence. As a modified tripeptide, it incorporates both a canonical amino acid and a non-canonical, methylated D-tryptophan residue, contributing to unique physicochemical properties and potential for specialized interactions with biological targets. The inclusion of D-2-methyltryptophan introduces steric and electronic modifications that can affect peptide conformation, stability, and recognition by enzymes or receptors. Such features make this compound of particular interest in peptide research, structural biology, and the development of molecular probes.
Peptide structure-activity relationship (SAR) studies: Modified peptides like His-[D-2-ME-Trp]-Ala are valuable tools in elucidating the relationship between peptide sequence, stereochemistry, and biological function. The incorporation of a D-amino acid and methyl group allows researchers to systematically investigate how such modifications influence peptide-receptor interactions, enzymatic stability, and conformational preferences. These insights are instrumental in the rational design of peptides with enhanced biological activity, selectivity, or resistance to proteolytic degradation.
Enzyme substrate specificity assays: The presence of non-canonical amino acids, such as D-2-methyltryptophan, makes this peptide a suitable substrate or inhibitor candidate in studies of protease and peptidase specificity. By challenging enzymatic systems with modified peptides, researchers can map substrate recognition motifs, identify cleavage preferences, and explore the mechanistic basis of enzyme selectivity. Such assays are critical for understanding the molecular determinants of peptide processing and for engineering enzymes with tailored specificities.
Peptide stability and degradation research: The unique structural features of His-[D-2-ME-Trp]-Ala, particularly the D-configuration and methylation, confer increased resistance to proteolytic degradation compared to peptides composed solely of L-amino acids. This property supports its use in experimental models aimed at investigating the metabolic stability of peptides, optimizing peptide half-life, and evaluating the impact of structural modifications on peptide turnover in biological systems.
Analytical method development: Synthetic peptides with defined modifications serve as standards or test analytes in the development and validation of analytical techniques, including high-performance liquid chromatography (HPLC), mass spectrometry, and capillary electrophoresis. His-[D-2-ME-Trp]-Ala can be utilized to assess method sensitivity, resolution, and selectivity for detecting small peptides and distinguishing between isomeric or modified forms, thereby supporting robust analytical workflows in peptide research laboratories.
Peptide-based probe and ligand development: The distinctive sequence and modifications in this tripeptide make it a candidate for the design of molecular probes, affinity ligands, or scaffolds for further functionalization. Researchers may employ such peptides to develop tools for target identification, binding assays, or as starting points for constructing libraries of bioactive peptides with tailored properties. The chemical versatility afforded by the D-2-methyltryptophan residue expands the utility of this compound in innovative research applications seeking novel peptide-based functionalities.
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