Fmoc-2,5-Dichloro-D-Phenylalanine is a protected, non-natural amino acid derivative in which the amino acid backbone bears an Fmoc (9H-fluoren-9-ylmethoxycarbonyl) carbamate on the alpha-amino group and a side chain based on D-phenylalanine substituted with two chloro atoms at the 2- and 5-positions of the aromatic ring. The molecule contains both a free carboxylic acid functional group and an aromatic chlorinated side chain that provides increased electron-withdrawing character and altered hydrophobicity relative to unsubstituted phenylalanine, while retaining the D stereochemical configuration indicated in the name. In peptide chemistry, the Fmoc-protected amino group supports stepwise assembly of peptide intermediates under protection-controlled conditions, and the 2,5-dichloro aromatic motif provides a defined handle for structure-activity studies, conformational probing, and analytical differentiation of chlorinated phenylalanine analogues.
CAT No: CP12207
Fmoc-2,5-Dichloro-D-Phenylalanine is an Fmoc-protected, D-configured phenylalanine derivative bearing two chlorine substituents at the 2- and 5-positions of the aromatic ring. The molecule contains the Fmoc carbamate on the amino functionality, a free carboxyl group suitable for peptide coupling, and a stereogenic center at the alpha carbon that preserves D-amino acid stereochemistry during synthesis. The electron-withdrawing chlorinated aryl side chain modulates aromatic reactivity and can influence coupling outcomes, protecting-group compatibility, and downstream derivatization of the phenyl ring. The combination of an orthogonally removable N-protecting group (Fmoc) with a halogenated aromatic motif makes this compound a practical chiral building block and intermediate for protected amino acid chemistry and peptide science.
1. Peptide Synthesis
Fmoc-2,5-Dichloro-D-Phenylalanine is applied in solid-phase peptide synthesis and automated peptide assembly where an Fmoc-protected, D-amino acid building block is required. The Fmoc carbamate enables standard base-mediated deprotection to generate a reactive amino group for sequential coupling, while the free carboxyl group participates in amide bond formation under peptide coupling chemistries. The D-configuration at the alpha carbon supports stereochemically defined incorporation into peptide chains, which is relevant for producing D-residue-containing peptides and stereochemically constrained analogs. The 2,5-dichloro substitution on the phenyl side chain provides an aryl handle that can tune hydrophobicity and aromatic electronics in the resulting peptide scaffold. Peptide building block preparation using this halogenated aromatic amino acid can support structure-activity relationship studies and reproducible synthesis of peptidic and peptidomimetic sequences.
2. Peptidomimetics And SAR
Fmoc-2,5-Dichloro-D-Phenylalanine is utilized in medicinal chemistry workflows focused on peptidomimetics and structure-activity relationship studies where aromatic halogen patterns are used to modulate molecular recognition. The chlorinated phenyl side chain provides a defined substitution pattern that can affect conformational preferences, binding-site interactions, and metabolic stability trends in SAR series, while the D-amino acid stereocenter supports systematic stereochemical variation. Fmoc protection supports stepwise assembly into peptide analogs or constrained scaffolds, enabling controlled incorporation of the halogenated aryl residue at a specific position within a sequence. The resulting peptide or peptide-like intermediate can then be carried forward to generate analog libraries for comparative binding or stability evaluations in a research setting. Amino acid derivatization strategies that preserve the D-configuration and maintain coupling-ready functional groups align with downstream molecular scaffold development.
3. Side-Chain Functionalization
Fmoc-2,5-Dichloro-D-Phenylalanine is suitable for synthetic organic chemistry routes that convert halogenated aromatic residues into further functionalized side-chain motifs. The 2,5-dichloro pattern provides two electrophilic aryl chloride sites that can potentially undergo selective cross-coupling or nucleophilic aromatic substitution depending on the chosen conditions and orthogonality requirements relative to the Fmoc group. The presence of the Fmoc-protected amine and carboxyl functionality supports staged synthesis, where N-deprotection and peptide coupling can be performed before halogen-based transformations at the aromatic ring. The D-stereocenter remains a stable stereochemical element through typical aryl functionalization steps, enabling stereodefined chiral intermediates for subsequent diversification. Downstream formation of substituted aryl derivatives from this amino acid can support fragment expansion, scaffold tuning, and fine chemical synthesis of chlorinated-to-functionalized aromatic analogs.
4. Chemical Biology Labeling
Fmoc-2,5-Dichloro-D-Phenylalanine is applied in chemical biology and biomolecule modification strategies where halogenated aromatic residues serve as chemically addressable features within peptides or protein fragments. The Fmoc-protected amino group supports incorporation into peptides that can later be used for conjugation workflows, while the chlorinated phenyl side chain can serve as a distinct structural tag for spectroscopic or chromatographic discrimination in analytical research. D-amino acid incorporation can also be used to adjust proteolytic stability of labeled peptides, supporting longer-lived probes in biochemical assays without changing the core coupling chemistry. The free carboxyl group enables amide formation during peptide construction, after which the resulting labeled peptide can be conjugated to carriers, surfaces, or affinity handles using standard functional group chemistries. This amino acid-based intermediate therefore supports downstream probe generation and molecular recognition studies that rely on defined aromatic substitution patterns and stereochemical control.
5. Pharmaceutical Intermediate Preparation
Fmoc-2,5-Dichloro-D-Phenylalanine is relevant to pharmaceutical intermediate preparation and specialty chemical production where halogenated, stereodefined amino acid derivatives are required for manufacturing-grade peptide building blocks. The Fmoc protecting group provides a robust N-protection strategy that is compatible with peptide coupling cycles and can be removed when transitioning from intermediate synthesis to final assembly steps. The D-configuration and chlorinated aromatic side chain allow controlled generation of chiral, halogenated residues that can be incorporated into process-ready peptide intermediates for downstream synthesis of peptidic drug candidates or analogs. The functional group set, including the carboxyl group for coupling and the protected amine for handling, supports scalable synthetic planning where intermediate isolation and purification are aligned with protected amino acid chemistry. Industrial chemistry routes that require stereochemically consistent building blocks can employ this compound to prepare well-defined intermediates for subsequent peptide construction and functionalization steps.
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