D-9-AnthrylaAlanine is a D-configured, non-proteinogenic amino acid derivative bearing an anthrylmethyl substituent on the side chain, classifying it as an anthracene/anthracene-like aromatic amino acid analogue used for chemical labeling studies. The molecule contains a free amino group and a carboxyl functional group and features the aromatic anthryl moiety as a hydrophobic, π-conjugated side-chain handle, with the D stereochemical designation indicating the configuration at the amino acid carbon. In research workflows, this compound is used as a fluorescent or chromophoric amino acid building block for preparing labeled peptides and for analytical method development where an anthryl group provides spectroscopic readout or a reactive tag for subsequent conjugation.
CAT No: CP20202
D-9-AnthrylaAlanine is a D-configured anthracene-derived amino acid bearing a chiral alpha carbon and a side chain substituted with an anthryl group at the 9-position. The molecule presents a primary amino functionality and a carboxylic acid (or readily addressable acid/amine reactivity depending on salt or protection state), enabling conversion into peptide-grade derivatives through standard amino acid coupling chemistry. The extended polyaromatic anthracene motif provides strong chromophoric and hydrophobic character, which can be exploited for fluorescence-based tracking, spectroscopic quantification, and noncovalent binding studies. The stereochemical integrity of the D-amino acid center supports preparation of stereodefined peptide analogs and chiral chemical biology probes.
1. Peptide Synthesis
D-9-AnthrylaAlanine is applied in peptide building block preparation where the D-amino acid stereocenter and the anthracene side chain must remain intact during coupling. The amino acid backbone supports conversion to N-protected, C-activated forms for peptide coupling, while the carboxyl functionality participates in amide bond formation to install the residue at a defined position. The anthryl substituent functions as a spectroscopic tag within peptide sequences, enabling monitoring of assembly steps and downstream characterization of peptide fragments. D-9-AnthrylaAlanine-derived peptides can be used to generate stereodefined constructs for mechanistic studies and structure-activity relationship investigations in peptide science.
2. Chemical Biology Probes
D-9-AnthrylaAlanine is utilized for chemical biology research that benefits from an anthracene chromophore integrated into an amino acid framework. The aromatic anthryl group can serve as a fluorescence or UV-visible reporter, while the D-configuration can influence peptide conformation, protease recognition, and binding modes in biomolecular assays. The amino and carboxyl functionalities enable derivatization into peptide conjugates, linkers, or immobilizable handles that preserve the chiral center during probe synthesis. D-9-AnthrylaAlanine can thereby be applied to generate molecular probes for studying biomolecular interactions, transport, and binding-site environments using spectroscopic readouts.
3. Side-Chain Functionalization
D-9-AnthrylaAlanine is suitable for side-chain functionalization workflows where the anthracene moiety is retained as a reactive or label-bearing aromatic scaffold. The compound's primary amino and carboxylic acid groups can be orthogonally protected to allow selective transformations on the anthryl-containing residue, including formation of N-derivatives for controlled reactivity and subsequent conjugation. The chiral alpha stereocenter enables stereodefined incorporation into modified amino acid analogs used in synthetic organic chemistry and peptide analog generation. D-9-AnthrylaAlanine derivatives can be further elaborated into functional intermediates for labeling strategies, affinity reagents, and spectroscopically active materials.
4. Analytical Research Standards
D-9-AnthrylaAlanine is employed as an analytical research standard and reference component in methods that require a defined chiral anthracene-containing amino acid. The combination of a stereochemically defined D-amino acid and a strongly absorbing aromatic chromophore supports detection by UV-visible spectroscopy and can facilitate method development for amino acid derivatization and peptide fragment analysis. The presence of both amine and acid functionalities enables conversion into derivatized standards compatible with chromatographic workflows and mass spectrometric characterization. D-9-AnthrylaAlanine can therefore support calibration, identity confirmation, and impurity profiling during peptide building block preparation and downstream peptide synthesis.
5. Pharmaceutical Intermediate Preparation
D-9-AnthrylaAlanine is applied as a chiral synthetic intermediate for manufacturing-oriented synthesis of anthracene-tagged amino acid derivatives used in research supply chains. The D-amino acid backbone can be transformed into protected amino acid intermediates, including N-protected derivatives and activated acid forms, to support controlled peptide coupling chemistry in fine chemical production. The anthryl aromatic group provides a stable motif for downstream incorporation into peptidomimetic scaffolds, linker systems, or assay reagents used during lead optimization. D-9-AnthrylaAlanine thus functions as a stereodefined precursor that aligns with process chemistry needs for reproducible amino acid derivative handling and subsequent conversion into peptide-grade materials.
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