D-Quinoylalanine is a D-configured, non-proteinogenic amino acid derivative featuring a quinoyl-substituted side chain attached to the α-amino acid backbone. The molecule contains an α-amino group and a carboxyl group that can participate in standard amino acid salt formation or coupling chemistry, while the quinoyl functionality provides an aromatic, conjugated handle that can influence electronic properties and potential binding or labeling behavior in chemical biology workflows. D-Quinoylalanine is used in peptide and small-molecule synthesis and structure-activity or labeling studies where a quinoyl-bearing amino acid analog is required to introduce a defined aromatic substituent and stereochemical form into larger constructs.
CAT No: CP23602
D-Quinoylalanine is a D-configured quinoyl-substituted alanine derivative in which the amino acid stereocenter is fixed at the D-configuration, enabling stereochemically defined peptide and peptidomimetic construction. The molecule contains a carboxylate functionality and an amino group that are typically handled under protection/deprotection strategies to control chemoselective coupling and minimize side reactions during synthesis. The quinoyl (quinoline-like) aromatic system introduces a rigid, π-rich heteroaromatic motif that can participate in noncovalent interactions and supports downstream derivatization for labeling, conjugation, or scaffold diversification. As a chiral amino acid intermediate, D-Quinoylalanine can be incorporated into amide linkages and can serve as a stereodefined building block for generating D-amino acid containing sequences and structure-defined analogs for biochemical and materials-oriented studies.
1. Peptide Synthesis
D-Quinoylalanine is used in peptide synthesis as a D-amino acid building block for constructing stereochemically defined amide bonds in D-peptide and mixed D/L-peptide frameworks. The carboxyl and protected amine functionality can be aligned with standard peptide coupling chemistries, while the quinoyl aromatic side motif remains compatible with typical orthogonal protection strategies that preserve the heteroaromatic integrity. Incorporation of the D-configuration can modulate backbone conformation and protease resistance profiles of the resulting peptide analogs, supporting peptide construction for mechanistic studies and scaffold optimization. Downstream, the quinoyl side chain can be leveraged for further functionalization of peptide conjugates and for generating peptide libraries where stereochemistry and aromatic recognition elements are controlled.
2. Peptidomimetics And SAR
D-Quinoylalanine is applied in peptidomimetic design and structure-activity relationship studies where a D-configured alanine core bearing a quinoyl heteroaromatic substituent enables systematic exploration of spatial and electronic effects. The rigid quinoyl aromatic system provides a defined hydrophobic and π-interaction surface, while the amino acid backbone supports controlled placement of the side chain through amide coupling. Protection of the amino and carboxyl functionalities during synthesis supports selective generation of analog series that vary only in stereochemistry or side-chain substitution patterns. The resulting D-amino acid containing peptidomimetics can be used as defined chemical probes for mapping binding determinants and for refining molecular recognition models in medicinal chemistry workflows.
3. Chemical Biology Probes
D-Quinoylalanine is suitable for chemical biology research requiring aromatic, stereodefined amino acid probes that can be incorporated into peptides, linkers, or recognition elements. The quinoyl heteroaromatic motif can function as a handle for noncovalent binding, fluorescence-compatible scaffolding, or affinity-based recognition depending on the conjugation strategy used in the downstream derivative. The D-configuration supports the creation of protease-stable probe constructs where stereochemical inversion relative to common L-amino acids can be used to probe mechanism-linked specificity. The amino acid intermediate nature of D-Quinoylalanine enables preparation of labeled or conjugatable analogs for studying molecular interactions and for generating defined probe panels in biochemical assay development.
4. Bioconjugation Chemistry
D-Quinoylalanine is employed in bioconjugation chemistry as a chiral aromatic amino acid component that can be introduced into conjugates through peptide-bond formation or linker assembly. The presence of an amino acid backbone with a carboxyl functionality supports conversion to activated intermediates or coupling-ready derivatives, while the quinoyl aromatic system can serve as a stable conjugation-bearing moiety that tolerates common aqueous-compatible handling after appropriate protection management. D-configured incorporation can influence solubility, steric presentation, and binding orientation of the conjugate, which is relevant for constructing stereodefined biomolecule conjugates. Downstream products can include peptide-tagged conjugates, affinity reagents, and scaffolded linkers used for biomolecule labeling and molecular recognition studies.
5. Pharmaceutical Intermediate Preparation
D-Quinoylalanine is applied as a pharmaceutical intermediate in fine chemical synthesis where stereodefined D-amino acid fragments are required for manufacturing peptide-like building blocks. The quinoyl-substituted alanine framework can be carried through protected amino acid synthesis routes, enabling controlled formation of amide linkages and subsequent deprotection to furnish coupling-ready intermediates. The heteroaromatic side chain can be retained through process-compatible protection strategies, supporting downstream assembly of D-amino acid containing intermediates for drug discovery chemistry and development pipelines. The compound's defined stereochemistry and functional group set make it suitable for producing structured analogs and for scaling chiral amino acid derivative manufacturing steps that require reliable chemoselective transformations.
6. Analytical Standards Development
D-Quinoylalanine is utilized in analytical research for developing stereochemically defined standards and reference materials for amino acid derivative characterization. The D-configuration and quinoyl heteroaromatic motif provide a distinctive chromatographic and spectrometric signature that can support method development for chiral analysis, peptide hydrolysate profiling, or monitoring of protected amino acid intermediates. Carboxyl and amino functionalities enable preparation of derivative standards aligned with the analytical workflow, including conversion to coupling analogs or protected forms that match sample matrices. The resulting reference utility supports robust identification and quantification of D-amino acid containing species in synthetic process monitoring and in biochemical sample analysis.
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