Boc-3,5-Dichloro-D-Phenylalanine is a protected, non-natural amino acid derivative featuring a D-configuration at the α-carbon and a benzyl side chain substituted with chlorine atoms at the 3 and 5 positions. The molecule contains a Boc-protected amino group and an unprotected carboxylic acid, while the dichloro-substituted phenyl ring provides increased hydrophobic character and steric modulation relative to unsubstituted phenylalanine. This protected analogue is used in peptide synthesis and related structure-activity studies where stepwise coupling requires amino protection and where the 3,5-dichloro phenyl side chain can be incorporated to probe effects of aromatic halogenation on peptide conformation, binding interactions, or analytical behavior.
CAT No: CP12505
Boc-3,5-Dichloro-D-Phenylalanine is a Boc-protected D-phenylalanine derivative bearing two chloro substituents at the 3 and 5 positions of the aromatic ring. This non-proteinogenic, halogenated amino acid building block is routinely used in peptide and peptidomimetic synthesis where steric and electronic effects from the dichloro phenyl side chain are leveraged for structure-activity relationship studies and conformational/interaction tuning. The Boc group provides a protected, acid-stable amino functionality that supports routine downstream coupling workflows for assembling modified peptide segments.
1. Peptide Building Block Use
Boc-3,5-Dichloro-D-Phenylalanine is used by peptide chemists to introduce a halogenated D-phenylalanine residue into synthetic peptide fragments and full-length analogs. The dichloro-substituted aromatic side chain is valuable for SAR campaigns that probe how increased hydrophobicity, altered aromatic electronics, and steric bulk influence binding or overall peptide behavior. The D-configuration supports incorporation of stereochemical features that are commonly explored in protease-resistant or non-native peptide architectures, while the Boc protection enables reliable handling and segment assembly in custom peptide synthesis workflows.
2. Peptidomimetic SAR Development
Boc-3,5-Dichloro-D-Phenylalanine serves as a specialized intermediate for medicinal chemistry teams building peptidomimetics and constrained peptide-like scaffolds. Halogenated phenylalanine analogs are frequently selected to modulate lipophilicity and aromatic interaction patterns in lead optimization, and the presence of two chloro substituents provides a distinct substitution pattern compared with mono-halogenated or unsubstituted phenylalanine derivatives. By enabling controlled incorporation of this stereodefined, electronically tuned residue, the reagent supports iterative structure-activity relationship studies in parallel synthesis and analog library generation.
3. Pharmaceutical Intermediate Synthesis
Boc-3,5-Dichloro-D-Phenylalanine is also used as a chiral amino acid intermediate for downstream preparation of substituted aromatic amino acid derivatives and related building blocks used in specialty chemical manufacturing. In this context, the protected amino functionality allows the material to be carried through multi-step synthetic sequences where the dichloro phenyl ring must remain intact for later functionalization or final coupling. Process and development chemists value the defined stereochemistry and substitution pattern when designing downstream intermediates for peptide-derived leads, linker modules, and other modular fragments used in research-scale synthesis.
4. Solid-Phase Peptide Assembly
Boc-3,5-Dichloro-D-Phenylalanine is employed in solid-phase peptide synthesis workflows to incorporate a defined halogenated residue during stepwise chain elongation. Researchers use this building block to generate peptide analogs that contain non-natural aromatic substitution patterns, supporting studies that relate side-chain electronics and steric effects to physicochemical properties and structure-function relationships. The Boc-protected amino group supports standard peptide assembly handling, enabling consistent incorporation of the D-configured dichloro phenylalanine unit into peptide sequences for analytical characterization and iterative optimization.
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