H-Gly-D-Gln-OH introduces a D-residue into a flexible dipeptide framework, supporting stereochemical and folding studies. The sequence reveals effects of chirality on hydrogen bonding and enzymatic recognition. Researchers assess its solubility and conformational transitions. Uses include motif analysis, D-amino acid incorporation studies, and structural modeling.
CAT No: R2505
CAS No:115588-13-1
Synonyms/Alias:H-Gly-D-Gln-OH;glycyl-d-glutamine;115588-13-1;gly-d-gln;MFCD00237909;AKOS037651059;CS-15794;FG108247;CS-0045258;D72201;(2R)-2-(2-AMINOACETAMIDO)-4-CARBAMOYLBUTANOIC ACID;
H-Gly-D-Gln-OH is a synthetic dipeptide composed of glycine and D-glutamine, representing a specialized tool in peptide research and biochemical investigations. As a member of the peptide compound category, it features a unique configuration due to the presence of the D-enantiomer of glutamine, which imparts distinct physicochemical and biological properties compared to its L-counterpart. The molecule's structural simplicity, combined with stereochemical specificity, makes it valuable for probing fundamental aspects of peptide behavior, stability, and function. Its relevance extends across studies in enzymology, peptide therapeutics development, and the exploration of D-amino acid-containing motifs in biological systems.
Peptide synthesis research: H-Gly-D-Gln-OH serves as a model substrate in the development and optimization of peptide synthesis methodologies. The incorporation of a D-amino acid residue challenges conventional coupling strategies and provides a rigorous test for the stereochemical fidelity of synthetic protocols. Researchers utilize this dipeptide to assess racemization risks, evaluate protecting group strategies, and refine solid-phase or solution-phase synthesis techniques. Its use supports the creation of more complex peptides containing D-amino acids, which are increasingly important in the design of protease-resistant biomolecules and novel peptide-based materials.
Enzymatic specificity studies: The dipeptide is frequently employed in investigations of protease and peptidase substrate specificity, particularly to elucidate the impact of D-amino acid residues on enzymatic recognition and cleavage. By comparing the hydrolysis rates and binding interactions of H-Gly-D-Gln-OH with those of analogous L-dipeptides, scientists gain critical insights into the stereochemical preferences of various enzymes. These studies contribute to a deeper understanding of enzyme-substrate interactions and inform the design of substrates or inhibitors with tailored properties.
Peptide conformational analysis: The presence of a D-amino acid within H-Gly-D-Gln-OH enables detailed studies on the conformational dynamics and structural properties of small peptides. Researchers utilize techniques such as nuclear magnetic resonance (NMR) spectroscopy, circular dichroism (CD), and computational modeling to investigate how D-residues influence peptide backbone geometry, hydrogen bonding patterns, and overall stability. Such analyses are fundamental for elucidating the structural determinants that govern peptide folding and function, especially in the context of designing peptidomimetics or studying naturally occurring D-amino acid-containing peptides.
Peptidomimetic design: The dipeptide is a valuable scaffold for the development of peptidomimetics, which are synthetic molecules designed to mimic the structure and function of natural peptides while exhibiting enhanced stability or altered biological activity. Incorporation of D-glutamine in the sequence imparts resistance to proteolytic degradation, a desirable feature in the engineering of peptide-based probes, inhibitors, or biomaterials. Researchers leverage H-Gly-D-Gln-OH as a building block or reference compound in the rational design and synthesis of novel peptidomimetics with improved pharmacokinetic or biophysical properties.
Analytical method development: H-Gly-D-Gln-OH is also utilized as a reference standard or calibration substrate in the development and validation of analytical techniques for peptide characterization. Its defined composition and stereochemistry make it suitable for evaluating chromatographic separation parameters, mass spectrometric detection, and quantitative amino acid analysis protocols. These applications are essential for ensuring the accuracy and reproducibility of peptide analysis workflows in both research and quality control environments.
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