DL-Quinoylalanine is a non-proteinogenic, quinoyl-substituted amino acid derivative featuring an amino acid backbone with a quinoyl (quinoline-like) aromatic side-chain that replaces the typical canonical side-chain functionality. The molecule contains a primary amino group and a carboxyl group, with the side chain bearing an extended conjugated aromatic system that can participate in π-π interactions and provides a distinct chemical handle for structural and labeling studies, while the "DL-" designation indicates a racemic mixture of stereoisomers at the amino acid stereocenter when present. DL-Quinoylalanine is used as a substrate or building block in peptide and peptidomimetic synthesis to introduce an aromatic quinoyl motif for structure-activity and binding-chemistry investigations, and it can also be employed in analytical method development where the quinoyl chromophore supports detection or differentiation of amino acid-containing materials.
CAT No: CP23603
DL-Quinoylalanine is a quinoyl-substituted alanine derivative presented as a racemic (DL) mixture, combining an amino acid backbone with a quinone-like aromatic functionality. The molecule contains the stereochemically relevant alanine alpha-carbon, a primary amino group that is typically handled through protection during synthesis, and a carboxyl group that can be converted into activated derivatives or ester forms for coupling chemistry. The quinoyl/aromatic moiety introduces redox-active and conjugation-capable reactivity that can participate in electrophilic aromatic substitution, nucleophilic addition to activated carbonyl-like sites, and oxidative transformations under controlled conditions. As a chiral amino acid intermediate precursor in DL form, DL-Quinoylalanine can be routed into protected amino acid synthesis and downstream peptide building block preparation, enabling access to quinoyl-bearing peptide analogs and functionalized aromatic scaffolds.
1. Peptide Synthesis
DL-Quinoylalanine is applied in peptide synthesis workflows where an amino acid building block with an aromatic quinoyl side functionality is required for peptide coupling and subsequent scaffold diversification. The alanine backbone supports standard N-protection and C-activation strategies, while the quinoyl group can be preserved or selectively transformed depending on the chosen protecting-group scheme and oxidation sensitivity. Incorporation into peptide chains enables construction of quinoyl-functionalized peptides that can be further modified through side-chain derivatization, including conjugation handles or redox-responsive motifs. Downstream peptide analogs prepared from DL-Quinoylalanine can serve as research-grade intermediates for studying how aromatic quinoyl substitution patterns influence peptide conformation and chemical reactivity.
2. Amino Acid Derivatization
DL-Quinoylalanine is used for amino acid derivatization and chemical modification chemistry aimed at generating quinoyl-bearing intermediates for fine chemical synthesis. The presence of a carboxylic acid and an amino group supports conversion into peptide coupling reagents, amino acid esters, or activated amides, while the quinoyl aromatic functionality enables additional functionalization steps such as nucleophile addition or controlled oxidative conversion to alter electrophilicity. Racemic DL material can be employed for library-style synthesis where stereochemical uniformity is not required, or can be resolved downstream if enantiopure material is needed for stereochemical SAR studies. Resulting derivatives can feed into broader amino acid derivatization routes that connect quinoyl aromatic chemistry with peptide-compatible functional group patterns.
3. Chemical Biology Probes
DL-Quinoylalanine is suitable for chemical biology research focused on molecular probes and reactive tags that incorporate a quinoyl aromatic motif into an amino acid context. The backbone amino and carboxyl functionality enables attachment to biomolecular scaffolds via amide formation, linker installation, or peptide-based conjugation strategies, while the quinoyl group provides a handle for redox- and conjugation-relevant reactivity. Incorporation into short peptides or peptidomimetic fragments can allow probe design where aromatic quinoyl substitution modulates binding interactions and chemical reactivity in complex media. Downstream probe derivatives prepared from DL-Quinoylalanine can be used as intermediates for analytical research and biomolecule modification studies requiring amino acid-derived chemical handles.
4. Peptidomimetics And SAR
DL-Quinoylalanine is applied in peptidomimetic construction and structure-activity relationship studies where aromatic quinoyl substitution is used to tune physicochemical properties and functional reactivity. The alanine alpha-carbon and side-chain quinoyl functionality support stereochemical exploration when paired with protected amino acid chemistry, including routes that generate defined stereoisomers after resolution or asymmetric synthesis from the corresponding chiral intermediates. The ability to convert the carboxyl group into coupling-ready forms and to protect the amine during assembly enables systematic generation of peptide analog series with consistent backbone chemistry. Downstream SAR-oriented libraries derived from quinoyl-bearing amino acid building blocks can be advanced into fragment-based molecular design and scaffold optimization programs in synthetic organic chemistry.
5. Pharmaceutical Intermediate Preparation
DL-Quinoylalanine is relevant to pharmaceutical intermediate preparation where amino acid-derived aromatic motifs are incorporated into processable intermediates for medicinal chemistry synthesis. The amino acid functional groups support manufacturing-compatible transformations such as N-protection, esterification, and conversion to activated carboxylic derivatives used in controlled coupling steps, while the quinoyl aromatic moiety can be carried through as a stable intermediate or converted into downstream electrophilic or conjugation-ready forms. Racemic DL starting material can be used in early-stage route development, with later stereochemical control introduced through resolution or asymmetric downstream steps when required for defined stereochemistry. Resulting quinoyl-containing intermediates can serve as feedstocks for fine chemical synthesis and industrial-scale preparation of peptide-like or aromatic-functionalized compounds.
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