L-9-Anthrylalanine is an L-configured, non-proteinogenic anthracene-derived amino acid bearing an anthryl group at the side chain position of alanine, resulting in a bulky polycyclic aromatic functionality. The molecule contains both an amino group and a carboxyl group characteristic of amino acids, with the aromatic 9-anthryl substituent providing a hydrophobic, π-conjugated handle suitable for fluorescence and photophysical studies, while retaining the stereochemical definition implied by the L designation. L-9-Anthrylalanine is used as a chemically defined building block for peptide and amino-acid derivative synthesis as well as for labeling, structure-activity studies, and analytical method development where an aromatic chromophore is incorporated into larger biomolecular constructs.
CAT No: CP20201
L-9-Anthrylalanine is an L-configured amino acid derivative in which the alanine backbone bears a 9-anthryl substituent on the side chain, providing a rigid polycyclic aromatic fluorophore-like motif alongside the primary amino and carboxylic acid functionalities. The stereogenic center at the alanine carbon maintains defined chirality for stereoselective peptide coupling and for chiral recognition in synthetic or analytical workflows. The aromatic anthracene-like system enables strong π-π interactions and can participate in photophysical and quenching-based assays, while the amino and acid groups support standard amino acid protection and activation chemistry. As an amino acid building block, it functions as a chemically addressable intermediate for peptide construction, aromatic side-chain functionalization, and downstream derivatization where controlled placement of the anthryl group is required.
1. Peptide Synthesis
L-9-Anthrylalanine supports peptide synthesis workflows by providing an L-amino acid backbone with a defined stereocenter and a side-chain anthracene-like aromatic handle. The carboxylic acid and amino group can be converted into peptide-compatible forms using N-protecting group strategies and carboxyl activation, enabling incorporation as a residue in linear peptides and peptide fragments. The bulky, conjugated anthryl side chain can influence coupling efficiency and steric outcomes, making it suitable for controlled formation of aromatic-containing peptide architectures. Downstream peptide analogs prepared from this residue can be used to probe side-chain effects on conformation, binding interfaces, and labeling behavior in structure-guided peptide design and chemical biology studies.
2. Fluorescent Probe Design
L-9-Anthrylalanine is applicable to chemical biology and analytical research as an anthryl-bearing amino acid that can function as a built-in aromatic reporter within peptides or small molecules. The rigid polycyclic aromatic side chain can undergo environment-dependent fluorescence changes and can participate in Förster resonance energy transfer or fluorescence quenching when positioned near other chromophores. N- and C-terminal modifications allow the anthryl motif to be placed at defined termini or internal positions, supporting probe construction for monitoring binding events, aggregation, or conformational transitions. Resulting labeled peptide probes and conjugates are useful for assay development, mechanistic interrogation, and orthogonal readouts in biochemical research where amino acid chemistry provides site-specific control.
3. Chiral Building Block Chemistry
L-9-Anthrylalanine serves as a chiral amino acid intermediate for stereoselective synthesis of anthryl-substituted derivatives used in molecular design and structure-activity relationship studies. The L-configuration at the alanine stereocenter enables predictable stereochemical outcomes during peptide coupling and during conversion to protected amino acid derivatives, including strategies that preserve stereochemical integrity through activation and coupling steps. Side-chain aromatic functionality can be retained while the amino acid groups are masked or transformed, supporting sequential derivatization into amide, ester, or protected amine intermediates. Chiral anthryl-containing products can then be employed to build enantiomerically defined libraries, evaluate stereochemical effects on molecular recognition, and generate reference compounds for analytical method development.
4. Bioconjugation Chemistry
L-9-Anthrylalanine can be utilized in bioconjugation and biomolecule modification by enabling site-controlled attachment of an anthryl aromatic motif to peptide-based handles. The amino acid functionality supports conversion to protected forms for controlled coupling, followed by deprotection to generate reactive amide-forming or coupling-ready intermediates depending on the conjugation strategy. The anthryl side chain can act as a tag for tracking, immobilization, or spectroscopic detection when incorporated into carrier peptides, affinity ligands, or labeling reagents. Downstream conjugates prepared from this building block can be applied in protein engineering workflows, receptor-ligand studies, and analytical characterization of biomolecular assemblies.
5. Pharmaceutical Intermediate Preparation
L-9-Anthrylalanine is suitable for fine chemical synthesis and pharmaceutical intermediate preparation where an anthryl-substituted amino acid scaffold is required for medicinal chemistry exploration. The presence of an L-amino acid backbone with a protected-amino/activated-acid logic supports conversion into key intermediates such as N-protected amino acid derivatives, peptide coupling partners, and aromatic side-chain-bearing fragments. The aromatic anthryl motif can be carried through synthetic sequences as a stable substituent for SAR studies, enabling systematic variation of linker length, steric environment, and aromatic placement. Resulting intermediates can feed into the construction of peptide-like inhibitors, peptidomimetic structures, and aromatic-tagged analogs used to map binding determinants in applied drug discovery chemistry.
6. Process Chemistry Intermediate
L-9-Anthrylalanine can be employed in process chemistry contexts as a chiral, aromatic amino acid intermediate that supports scalable synthesis of anthryl-containing building blocks. The amino acid functional group set enables robust protection and activation sequences that can be adapted to manufacturing routes for producing protected amino acid derivatives and coupling-ready intermediates. The chemically stable polycyclic aromatic side chain facilitates downstream handling during intermediate isolation and can be retained without requiring additional functional group transformations at the aromatic position. Industrially relevant use cases include specialty chemical production of chiral amino acid reagents for peptide manufacturing, labeled reagent generation for analytical workflows, and preparation of aromatic amino acid fragments for continued synthesis in multi-step fine chemical programs.
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