Boc-2-Chloro-D-Phenylalanine is a protected, non-natural amino acid derivative featuring a D-configuration at the alpha carbon and a 2-chloro substituent on the side chain of a phenylalanine framework. The molecule contains a Boc-protected amino group (tert-butoxycarbonyl) and a free carboxyl functional group, while the aromatic side chain bears a chloro substituent that can modulate polarity and participate in halogen-mediated interactions during peptide or conjugate construction. As a Boc-protected amino acid building block, it is used in stepwise peptide synthesis and related chemical biology workflows where controlled chemoselectivity of the amino functionality and incorporation of a halogenated aromatic residue are required for structure-activity or labeling studies.
CAT No: CP11405
CAS No:80102-23-4
Synonyms/Alias:Boc-2-chloro-D-phenylalanine;80102-23-4;Boc-D-2-Chlorophe;(R)-2-((tert-Butoxycarbonyl)amino)-3-(2-chlorophenyl)propanoicacid;Boc-D-2-Chlorophenylalanine;Boc-D-Phe(2-Cl)-OH;Boc-L-phe(2-Cl)-OH;ST51037516;(2R)-2-[(tert-butoxycarbonyl)amino]-3-(2-chlorophenyl)propanoicacid;(2R)-2-[(tert-butoxy)carbonylamino]-3-(2-chlorophenyl)propanoicacid;(R)-2-(TERT-BUTOXYCARBONYLAMINO)-3-(2-CHLOROPHENYL)PROPANOICACID;AC1ODUTA;KSC916S4B;15018_ALDRICH;BOC-O-CHLORO-D-PHE-OH;(Boc-L-2-Chlorophenylalanine);SCHEMBL3485116;BOC-D-2-CHLORO-PHE-OH;15018_FLUKA;CTK8B6940;MolPort-001-758-154;TUUQJNHCVFJMPU-LLVKDONJSA-N;ZINC2570191;ANW-54984;CB-732
Boc-2-Chloro-D-Phenylalanine is a D-configured, side-chain functionalized amino acid building block bearing a benzyl side chain substituted with a 2-chloro group and an N-terminal Boc protecting group. This protected amino acid is used in peptide and peptidomimetic synthesis workflows where a chloro-substituted aromatic side chain is required for subsequent derivatization, SAR studies, or incorporation into defined sequences. Its stereochemical purity and acid-stable Boc protection make it a practical intermediate for medicinal chemistry and custom peptide manufacturing.
1. Peptidomimetic Building Block
Boc-2-Chloro-D-Phenylalanine is used by medicinal chemistry and peptide chemistry groups to assemble peptidomimetic scaffolds that incorporate a D-amino acid residue with a chloro-substituted phenyl side chain. The Boc protection supports controlled coupling during protected-amino-acid assembly, while the 2-chloro substituent provides a chemically handle for downstream diversification, enabling structure-activity relationship (SAR) exploration in lead optimization programs. Researchers commonly select this residue when they want to introduce stereochemical differentiation and an aryl halide motif into a defined oligomer for subsequent functional mapping or analog generation.
2. SAR Derivatization Intermediate
Boc-2-Chloro-D-Phenylalanine serves as a practical pharmaceutical intermediate for preparing analog series where the aryl chloride functionality is retained for later substitution or cross-coupling chemistry. In small-molecule and peptide-conjugate development, the chloro group can be leveraged to introduce new substituents while maintaining the amino acid-derived backbone architecture established in the earlier synthetic stage. Teams developing halogenated aromatic residues for property tuning (e.g., electronic and steric effects within a peptide-like framework) often rely on this protected D-amino acid as a consistent, stereochemically defined starting point for parallel synthesis.
3. Custom Peptide Synthesis
Boc-2-Chloro-D-Phenylalanine is used in custom peptide manufacturing and research peptide synthesis to introduce a specific D-phenylalanine variant with an aryl chloride side chain into short peptides and modified sequences. The N-Boc protection supports stepwise assembly using standard protected-amino-acid strategies, allowing the chloro-substituted aromatic residue to be incorporated with defined stereochemistry for downstream characterization. Peptide chemists frequently choose this building block when the target sequence requires a halogenated aromatic side chain for later functionalization, analytical differentiation, or sequence-specific structure studies.
1. Autoinhibition and phosphorylation-induced activation of phospholipase C-γ isozymes
4. Cationic cell-penetrating peptides are potent furin inhibitors
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