Fmoc-2,6-Dichloro-D-Phenylalanine is an Fmoc-protected, non-natural amino acid derivative featuring a D-configuration at the alpha carbon and a phenylalanine backbone bearing two chlorine substituents at the 2 and 6 positions of the aromatic ring. The molecule contains an Fmoc carbamate protecting group on the amino functionality and a free carboxylic acid, while the 2,6-dichloro aromatic side chain provides increased hydrophobicity and steric/electronic modulation relative to unsubstituted phenylalanine. In peptide synthesis workflows, the Fmoc-protected amino acid is used as a building block for stepwise incorporation into peptide chains, and the halogenated aromatic side chain can serve as a handle for structure-activity studies, labeling strategies, or chemical probe design where aryl halogens are relevant.
CAT No: CP12307
Fmoc-2,6-Dichloro-D-Phenylalanine is an Fmoc-protected D-phenylalanine derivative bearing two chlorine atoms at the 2- and 6-positions of the aromatic ring, creating a sterically hindered, electronically modified side chain. The molecule contains a chiral α-carbon characteristic of D-phenylalanine, an Fmoc carbamate that serves as an orthogonally removable N-protecting group in peptide synthesis, and a carboxyl functionality presented as a protected amino acid building block suitable for coupling chemistry. The dichloro-substituted phenyl ring can participate in halogen-directed conformational effects and can undergo further derivatization routes such as cross-coupling or nucleophilic aromatic substitution after peptide assembly or at the intermediate stage. The overall reactivity profile is governed by the Fmoc-protected amine and the aryl chlorides, enabling controlled peptide incorporation while preserving handles for downstream synthetic transformations.
1. Peptide Synthesis
Fmoc-2,6-Dichloro-D-Phenylalanine is used in solid-phase peptide synthesis and related protected amino acid chemistry to introduce a D-phenylalanine stereocenter into peptide chains with a halogenated aromatic side chain. The Fmoc carbamate protects the α-amino group for stepwise peptide coupling, while the carboxyl functionality supports amide bond formation under standard peptide coupling conditions compatible with Fmoc strategies. The 2,6-dichloro substitution can influence local sterics around the side chain, which may affect peptide folding, backbone conformations, and resistance to proteolytic processing when incorporated as a D-amino acid. Downstream, the resulting peptidic products can serve as scaffold components for peptidomimetics and structure-guided optimization studies in biochemical research.
2. Peptidomimetics And SAR
Fmoc-2,6-Dichloro-D-Phenylalanine is applied in medicinal chemistry-oriented peptide analog construction where halogenated aromatic residues are used to tune lipophilicity, binding pocket complementarity, and conformational preferences. The D-configuration at the α-carbon provides stereochemical control that can modulate molecular recognition relative to L-analogues, while the 2,6-dichloro phenyl ring supplies a rigid, electron-withdrawing aromatic element with defined steric bulk. The Fmoc-protected amino acid format enables systematic incorporation into libraries for structure-activity relationship studies, including fragment-like substitution patterns on peptide backbones. The aryl chlorides can also function as latent synthetic handles for later diversification of peptidomimetic scaffolds, supporting iterative SAR workflows.
3. Side-Chain Functionalization
Fmoc-2,6-Dichloro-D-Phenylalanine is suitable for synthetic organic chemistry routes that leverage aryl chloride reactivity for post-assembly modification of amino acid-derived motifs. The dichloro-substituted phenyl side chain provides electrophilic aromatic positions that can potentially undergo cross-coupling chemistry or other substitution-based transformations after the amino acid has been incorporated into a peptide or retained as an intermediate. The Fmoc group enables orthogonal protection management, allowing selective deprotection and coupling while maintaining the aryl chlorides for later functional group installation. Resulting derivatives can include aryl-substituted analogs used to generate chemical probes, diversify binding interactions, or access new physicochemical profiles in applied research and specialty chemical synthesis.
4. Chemical Biology Probes
Fmoc-2,6-Dichloro-D-Phenylalanine is used in chemical biology research to prepare D-amino acid-containing peptides and peptidomimetics that act as molecular recognition probes. The combination of an Fmoc-protected α-amino group and a halogenated aromatic side chain supports controlled incorporation into probe scaffolds, where the D-stereochemistry can enhance stability against enzymatic degradation and maintain defined spatial presentation of the aromatic moiety. The 2,6-dichloro pattern can promote specific hydrophobic and halogen-interaction contributions within binding interfaces, aiding the design of probes for receptor-binding studies, enzyme substrate mimics, or interaction mapping. Downstream, probe derivatives can be further functionalized using the aryl chloride handles to introduce labels or reactive groups for subsequent conjugation workflows.
5. Pharmaceutical Intermediate Preparation
Fmoc-2,6-Dichloro-D-Phenylalanine is employed as a defined chiral intermediate in pharmaceutical manufacturing planning for the synthesis of halogenated peptide-like building blocks and related active ingredient precursors. The Fmoc-protected amino acid format supports reproducible coupling chemistry in manufacturing-scale peptide synthesis, while the D-configuration provides stereochemical fidelity for downstream drug discovery and process chemistry intermediate formation. The dichloro-substituted aromatic side chain can be retained through early stages to preserve a controlled substitution pattern, then transformed later in the route to reach targeted analog series. The compound's structure aligns with industrial fine chemical synthesis needs where protected amino acid derivatives, stereodefined intermediates, and functional-group-tunable scaffolds are required for scalable production of complex molecules.
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