Fmoc-2,4-Dichloro-D-Phenylalan is a protected, non-natural phenylalanine derivative in which the amino group is masked as an Fmoc carbamate and the aromatic side chain bears two chloro substituents at the 2- and 4-positions, classifying it as a halogenated amino acid building block. The molecule contains a free carboxyl group and an Fmoc-protected α-amino functionality, and its stereochemistry is specified as the D-configuration at the α-carbon, with the chlorinated benzyl side chain providing increased hydrophobicity and distinct electronic character compared with unsubstituted phenylalanine. In peptide synthesis workflows such as stepwise or solid-phase assembly, the Fmoc protection supports controlled chemoselective coupling while the 2,4-dichloro substitution provides a defined aromatic handle for structure-activity studies, chemical biology labeling strategies, and the preparation of halogenated peptide analogues and related intermediates.
CAT No: CP12107
Fmoc-2,4-Dichloro-D-Phenylalan is a D-configured, Fmoc-protected amino acid derivative featuring a benzyl side chain bearing two chlorine substituents at the 2- and 4-positions. The molecule contains an Fmoc carbamate on the amino group and a carboxylic acid functionality suitable for peptide coupling after activation, while the aromatic dichloro substitution pattern introduces increased hydrophobicity and distinctive electronic effects that can influence binding and conformational preferences in peptide-like scaffolds. The stereogenic center at the alpha-carbon enforces D-amino acid stereochemistry, supporting stereochemically defined incorporation into sequences and chiral structure construction. The aryl chlorides are stable under many standard peptide synthesis conditions yet can serve as handles for downstream derivatization, enabling further functionalization of the side chain after assembly or during medicinal chemistry optimization.
1. Peptide Synthesis
Fmoc-2,4-Dichloro-D-Phenylalan is applied in solid-phase peptide synthesis and related peptide building workflows where Fmoc chemistry enables controlled N-terminal protection and stepwise chain elongation. The Fmoc-protected amine and carboxylic acid group support standard peptide coupling strategies to install a D-configured residue into growing sequences. The 2,4-dichloro-substituted phenyl side chain can modulate local hydrophobicity and aromatic surface properties, which is relevant for assembling peptide analogs with altered folding propensity and protease resistance profiles. The resulting D-amino acid incorporation supports stereochemically defined peptide construction for downstream characterization and structure refinement in amino acid and peptide science.
2. Peptidomimetics And SAR Studies
Fmoc-2,4-Dichloro-D-Phenylalan serves as a chiral scaffold element for peptidomimetic design and structure-activity relationship studies that rely on systematic side-chain electronic and steric tuning. The dichloro aromatic pattern provides a defined substitution topology that can influence π-interactions, polarizability, and hydrophobic contacts when embedded in peptide-like frameworks. The D-configuration allows exploration of stereochemical effects on receptor or target recognition by generating analog series with controlled inversion at the alpha-center while keeping the side chain substitution constant. The aryl chloride substituents can further enable late-stage side-chain diversification, supporting iterative SAR mapping through amino acid derivatization and scaffold elaboration.
3. Side-Chain Functionalization
Fmoc-2,4-Dichloro-D-Phenylalan is suitable for synthetic organic chemistry routes that use the protected amino acid as a chiral intermediate for post-assembly side-chain modification. The benzene ring bearing two chloro substituents can participate in nucleophilic aromatic substitution or cross-coupling-based transformations after peptide deprotection or when the amino acid is used as a standalone intermediate. The Fmoc group provides orthogonal protection during early-stage coupling chemistry, allowing side-chain transformations to be scheduled after peptide assembly or after selective deprotection steps. The D-amino acid backbone ensures stereochemical integrity during downstream derivatization, enabling the generation of functionalized aromatic analogs for medicinal chemistry, biochemical probe development, and fine chemical synthesis.
4. Chemical Biology Probes
Fmoc-2,4-Dichloro-D-Phenylalan can be used in chemical biology workflows that require incorporation of a D-amino acid residue into labeled or affinity-tagged peptide constructs. The Fmoc-protected amine supports incorporation into peptide sequences for subsequent deprotection and conjugation chemistry, while the dichloro phenyl side chain can act as a hydrophobic/aromatic motif that improves retention in binding assays or probe scaffolds. The presence of aryl chloride substituents provides chemical handles for installing linkers, affinity groups, or reporter moieties through derivatization strategies compatible with peptide-derived materials. The stereodefined D-amino acid residue helps control stereochemical recognition and can support probe libraries used in biochemical research intermediate preparation and molecular recognition studies.
5. Pharmaceutical Manufacturing Intermediates
Fmoc-2,4-Dichloro-D-Phenylalan is relevant to pharmaceutical manufacturing and process chemistry as a protected amino acid intermediate for producing D-amino acid-containing peptide intermediates under scalable synthetic conditions. The Fmoc carbamate and carboxylic acid functionality align with established peptide coupling and deprotection logic used in industrial peptide manufacturing sequences. The dichloro aromatic side chain can support targeted scaffold generation for downstream active or investigational peptide-like materials, while the D stereocenter provides stereochemical control that is often required for consistent downstream properties. The compound's stable aryl chloride functionality can be leveraged for controlled downstream transformations during intermediate elaboration, supporting reliable route design in specialty chemical production and industrial chemical manufacturing.
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