DL-9-Anthrylalanine is a racemic (DL) anthracene-derived, non-proteinogenic amino acid analogue in which the alanine backbone bears a 9-anthryl substituent on the side chain, classifying it as an aromatic, bulky amino acid derivative suitable for peptide-related chemistry. The molecule contains a free amino group and a carboxyl functional group on the α-carbon framework, while the 9-anthryl moiety provides extended π-conjugation and hydrophobic/aromatic character that can influence solubility, stacking interactions, and spectroscopic behavior in analytical or labeling contexts. As a synthetic building block, DL-9-Anthrylalanine is used to prepare modified peptides and amino acid derivatives for structure-property studies, fluorescence/UV-active labeling experiments, and chemical biology workflows that require an anthryl chromophore-bearing residue.
CAT No: CP20203
DL-9-Anthrylalanine is a racemic anthracene-derived aromatic amino acid in which an anthryl group is attached to the alanine side chain, yielding a chiral amino acid framework with stereochemistry present as a DL mixture. The molecule contains the alanine-type primary amino functionality and a carboxylic acid (or acid-equivalent form depending on salt/derivative), enabling standard amino acid coupling chemistry to form amide bonds. The extended polycyclic aromatic anthryl moiety provides strong π-surface character and fluorescence-relevant photophysics, while the stereogenic center at the alanine carbon supports stereochemical studies when resolved or incorporated as a defined enantiomer. As an amino acid-based intermediate, DL-9-Anthrylalanine can be protected at the amine and/or converted to activated acid forms to support downstream peptide building block preparation and fine chemical synthesis.
1. Peptide Synthesis
DL-9-Anthrylalanine is applied in peptide coupling workflows where the amino acid backbone participates in amide bond formation to assemble anthryl-containing peptides and peptide fragments. The presence of the alanine carboxylic acid and primary amine enables conversion to N-protected derivatives and subsequent coupling using peptide coupling reagents, while the anthryl side-chain aromatic group remains compatible with typical protecting-group strategies. Racemic stereochemistry can be used to generate libraries of peptide analogs or to probe how side-chain aromatic placement affects conformational preferences and intermolecular interactions. Downstream, the anthryl-bearing peptide products can serve as research materials for binding assays, fluorescence-tagged peptide constructs, and method development for aromatic amino acid incorporation.
2. Chemical Biology Probes
DL-9-Anthrylalanine is utilized in chemical biology research to introduce a polycyclic aromatic reporter handle into peptides and small biomolecule conjugates. The anthryl group can function as a spectroscopic moiety for monitoring binding, local environment changes, or proximity effects when positioned at the alanine side chain within a larger scaffold. The amino acid functionality supports conjugation strategies after conversion to protected amino acid derivatives, enabling controlled attachment to carrier proteins, linkers, or reactive handles through amide formation. Resulting anthryl-labeled biomolecular constructs can be used as experimental probes for studying molecular recognition, interaction kinetics, and structure-dependent behavior in biochemical assays.
3. Chiral Building Block Development
DL-9-Anthrylalanine is relevant to chiral synthesis programs where the racemic amino acid serves as a starting point for enantiomer-directed studies and stereochemical assignment. The stereogenic center on the alanine carbon allows resolution or asymmetric downstream derivatization to access defined L- or D-configured anthrylalanine building blocks for stereocontrolled peptide construction. Protecting-group selection for the amine and carboxyl functionalities can be tailored to support sequential transformations, including activation of the acid for coupling or conversion to ester intermediates for controlled handling. Enantiopure derivatives derived from this racemate can then be incorporated into peptide analogs, peptidomimetics, or stereodefined SAR series to evaluate how absolute configuration influences molecular recognition and conformational outcomes.
4. Side-Chain Functionalization
DL-9-Anthrylalanine is applied in synthetic organic chemistry for side-chain and scaffold modification where the anthryl aromatic system provides a stable platform for further derivatization or incorporation into functional materials. The amino acid backbone can be protected and transformed into activated intermediates, enabling selective chemical elaboration while maintaining compatibility with peptide coupling chemistry. Functional group reactivity is guided by the amine and carboxylic acid positions, which can be masked as N-protected groups and activated as acid derivatives to control where subsequent linkages form. Downstream products include anthryl-containing amide-linked intermediates for fragment assembly, fluorescent or sensing motifs in small-molecule libraries, and process-ready building blocks for specialty chemical production.
5. Pharmaceutical Intermediate Preparation
DL-9-Anthrylalanine is suitable for pharmaceutical intermediate preparation where aromatic amino acid motifs are incorporated into peptidomimetic frameworks or used to generate structure-activity relationship (SAR) analogs. The compound's amino acid functionality supports conversion into protected amino acid derivatives and activated acid forms that can be used in stepwise synthesis toward amide-rich intermediates. The anthryl aromatic moiety can be retained through multiple synthetic stages, enabling downstream generation of analog series with consistent aromatic substitution patterns. Prepared intermediates can feed into fine chemical synthesis routes that require chiral amino acid handling, controlled deprotection, and reliable peptide-coupling compatibility for medicinal chemistry workflows.
6. Analytical Research Standards
DL-9-Anthrylalanine is used in analytical research as a reference material and derivatization component for monitoring amino acid incorporation, stereochemical outcomes, and peptide synthesis progress. The anthryl chromophore enables detection by UV/fluorescence-compatible methods, while the amino acid core provides direct relevance to chromatographic behavior of amino acid derivatives and peptide building blocks. Conversion into protected forms or coupling-ready intermediates can support method development for quantifying anthryl-containing peptides and related intermediates in complex reaction mixtures. Analytical standards derived from this racemate can therefore support quality control of amino acid derivative synthesis, characterization of peptide analogs, and development of robust analytical workflows for aromatic amino acid chemistry.
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