Fmoc-2,3-Dichloro-D-Phenylalanine is an Fmoc-protected, non-natural amino acid derivative featuring a D-phenylalanine backbone substituted with two chlorine atoms at the 2- and 3-positions of the aromatic ring. The molecule contains a free carboxyl group and a primary amino group masked by the Fmoc protecting group, while the dichloro-phenyl side chain provides increased hydrophobicity and halogen-bonding character relative to unsubstituted phenylalanine. As an activated protected amino acid building block, it is used in peptide synthesis workflows such as solid-phase or solution-phase assembly to introduce a halogenated aromatic residue for structure-activity studies, chemical biology labeling strategies, and the preparation of modified peptide analogues.
CAT No: CP12007
Fmoc-2,3-Dichloro-D-Phenylalanine is an Fmoc-protected D-phenylalanine derivative in which the α-carbon bearing the stereocenter is substituted with two chlorine atoms at the 2- and 3-positions, creating a halogenated amino acid scaffold with pronounced electron-withdrawing character. The molecule contains the Fmoc carbamate for temporary N-protection during peptide coupling, a free carboxyl functionality suited to activation chemistry, and a chlorinated side-chain region that can influence conformational preferences and reactivity toward nucleophiles. The D-configuration at the amino acid stereocenter supports stereochemically defined incorporation into peptide sequences and chiral structure construction. The dense halogenation pattern can participate in halogen-bonding interactions and can serve as a handle for downstream transformations such as selective dehalogenation, nucleophilic substitution, or conversion to other functional motifs under appropriate conditions.
1. Peptide Synthesis
Fmoc-2,3-Dichloro-D-Phenylalanine supports solid-phase peptide synthesis workflows where Fmoc protection enables controlled N-deprotection and subsequent amide bond formation. The D-phenylalanine backbone provides a stereodefined amino acid building block, while the 2,3-dichloro substitution can be carried through coupling steps without requiring side-chain protection beyond the inherent halogen stability under standard peptide assembly conditions. The free carboxyl group can be activated for peptide coupling, allowing incorporation as a residue that modulates local polarity, sterics, and halogen-bonding potential in the growing chain. The resulting halogenated peptide analogs are suitable for generating sequence-defined libraries and for studying how α/β-halogenated amino acid motifs affect peptide conformation and recognition.
2. Peptidomimetics And SAR Studies
Fmoc-2,3-Dichloro-D-Phenylalanine is well suited for peptidomimetic construction and structure-activity relationship studies because the chlorinated aromatic amino acid framework can tune hydrophobicity and electrostatic features relative to non-halogenated analogs. The Fmoc-protected N-terminus and carboxyl functionality allow systematic replacement of phenylalanine positions with a D-configured, halogen-rich residue in peptide-like scaffolds. The 2,3-dichloro pattern can act as a chemical "switch" that changes intermolecular interactions, enabling SAR campaigns focused on binding-site complementarity and conformational constraints. Downstream derivatives can be prepared by converting the halogenated motif into alternative functional groups, supporting iterative medicinal chemistry-style optimization of peptide analogs.
3. Chiral Building Block Synthesis
Fmoc-2,3-Dichloro-D-Phenylalanine serves as a chiral amino acid intermediate for stereoselective synthesis where the D-stereocenter provides a defined configuration for downstream chiral targets. The Fmoc carbamate offers a robust protecting-group strategy that can be removed when the intermediate is ready for coupling or further functionalization, supporting convergent synthesis planning in fine chemical routes. The dichloro substitution pattern can be leveraged as a reactive structural element, enabling subsequent derivatization steps such as nucleophilic substitution to introduce heteroatom-containing substituents or controlled dehalogenation to adjust aromatic/alkyl electronics. The compound's stereochemical integrity and functional-group layout make it suitable for constructing chiral, halogenated amino acid derivatives used as intermediates in complex synthetic programs.
4. Side-Chain Functionalization
Fmoc-2,3-Dichloro-D-Phenylalanine enables side-chain functionalization strategies in which the 2,3-dichloro motif provides defined leaving groups for substitution chemistry. The amino acid framework retains the carboxyl group and the D-configuration, while the Fmoc protection can be maintained during initial transformations and removed to expose the amine for subsequent coupling or conjugation. The chlorinated region can be converted into alternative substituents that introduce hydroxyl, amino, or other heteroatom functionalities, supporting generation of functionalized amino acid derivatives and labeled or reactive analogs. Downstream products formed from this halogen handle can be used to build new peptide analogs, to prepare chemical probes, or to generate intermediate sets for process development in specialty synthesis.
5. Chemical Biology and Bioconjugation
Fmoc-2,3-Dichloro-D-Phenylalanine can be applied in chemical biology workflows that require incorporation of a halogenated amino acid residue into peptides or protein fragments followed by chemical modification. The Fmoc-protected N-terminus supports peptide assembly into defined conjugation-ready sequences, while the dichloro substitution can provide a functional handle for post-assembly transformations that introduce conjugatable groups. The D-configuration can be used to control stereochemical presentation of the residue within biomolecule-binding motifs, which can influence labeling specificity and stability of the resulting conjugates. The compound therefore supports downstream generation of modified biomolecules, including peptide-based probes and conjugation intermediates used for mechanistic studies and molecular recognition investigations.
6. Pharmaceutical Intermediate Preparation
Fmoc-2,3-Dichloro-D-Phenylalanine is suitable for pharmaceutical intermediate preparation where halogenated amino acid building blocks serve as defined inputs for medicinal chemistry-style synthesis of peptide-like candidates. The Fmoc-protected amino group supports scalable, stepwise protection and deprotection logic, while the carboxyl functionality enables activation chemistry compatible with peptide coupling and intermediate conversion strategies. The 2,3-dichloro substitution can be retained to provide a specific physicochemical profile in final scaffolds or transformed into alternative functionalities to diversify chemical space during candidate refinement. The compound's clear stereochemical identity and protected amino acid format make it compatible with manufacturing-oriented route design for producing halogenated amino acid derivatives and peptide intermediates for further synthetic elaboration.
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