Boc-4-Iodo-L-Phenylalanine is a Boc-protected amino acid derivative featuring an L-phenylalanine backbone with an iodine substituent at the para position of the aromatic side chain, classifying it as an iodinated, non-natural aromatic amino acid building block. The molecule contains a Boc-protected α-amino group and a free carboxylic acid, with the iodo-phenyl side chain providing a halogenated aromatic functionality that can support chemoselective labeling or further derivatization while the stereocenter at the α-carbon is specified as L. In peptide chemistry, the Boc protection controls chemoselectivity during stepwise coupling by masking the amine, enabling its use as a precursor for preparing iodinated peptide analogues and for introducing an aryl iodide handle for subsequent synthetic or analytical workflows.
CAT No: CP15204
CAS No:62129-44-6
Synonyms/Alias:62129-39-9;(s)-n-boc-4-bromophenylalanine;Boc-L-4-Bromophenylalanine;boc-4-bromo-l-phenylalanine;boc-l-4-bromophe;boc-phe(4-br)-oh;boc-l-4-bromophenylalnine;(S)-3-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)propanoicacid;boc-p-bromo-phe-oh;N-Boc-4-bromo-L-phenylalanine;boc-4'-bromo-l-phe;boc-l-4-bromo-phe-oh;Boc-L-phe(4-Br)-OH;(2s)-3-(4-bromophenyl)-2-[(tert-butoxycarbonyl)amino]propanoicacid;BOC-L-4-BR-PHE-OH;(s)-3-(4-bromophenyl)-2-(tert-butoxycarbonylamino)propanoicacid;n-alpha-t-butyloxycarbonyl-4-bromo-l-phenylalanine;MFCD00237571;SBB063715;4-bromo-l-phenylalanine,n-bocprotected;(s)-3-(4-bromo-phenyl)-2-tert-butoxycarbonylamino-propionicacid;Boc-D-phe(4-Br)-OH;(S)-BOC-2-AMINO-3-(4-BROMOPHENYL)PROPIONICACID;N-ALPHA-(T-BUTOXYCARBONYL)-4-BROMO-L-PHENYLALANINE;(2S)-2-[(tert-butoxy)carbonylamino]-3-(4-bromophenyl)propanoicacid
Boc-4-Iodo-L-Phenylalanine is a Boc-protected L-phenylalanine derivative bearing an iodine substituent on the para position of the aromatic ring. As a protected amino acid building block, it is designed for incorporation into peptide segments during protected-amino-acid synthesis workflows, while the aryl iodide provides a functional handle for downstream diversification via palladium-catalyzed coupling. This combination makes it useful for preparing iodinated peptide intermediates and aryl-substituted peptide analogs used in medicinal chemistry and chemical biology studies.
1. Peptide Building Block Synthesis
Boc-4-Iodo-L-Phenylalanine is used by peptide chemists and custom synthesis groups to assemble peptide fragments that require a para-iodo phenylalanine residue. The Boc protection supports controlled amino-group chemistry during protected-amino-acid workflows, enabling reliable segment coupling when building longer sequences or preparing modified analog libraries. The para-iodo substituent is retained through peptide assembly so that the iodinated aromatic side chain can be carried forward into final peptide targets or used as an intermediate for later structural diversification.
2. Medicinal Chemistry SAR Diversification
Boc-4-Iodo-L-Phenylalanine is commonly selected in medicinal chemistry for generating iodinated peptide and peptidomimetic scaffolds that can be diversified into aryl-substituted analogs. The aryl iodide serves as a coupling-ready functional group for introducing substituents on the aromatic ring after peptide construction, supporting structure-activity relationship (SAR) exploration where small changes on the para position are used to tune properties such as physicochemical character and binding-site interactions. Research groups use this approach to rapidly access series of analogs while keeping the peptide backbone and stereochemical integrity consistent across the library.
3. Chemical Biology Probe and Tagging Intermediates
Boc-4-Iodo-L-Phenylalanine is also used as a practical intermediate for preparing iodinated peptide probes and labeling precursors in chemical biology workflows. The retained para-iodo handle allows subsequent attachment of aryl-functional moieties, including linkers or reporter-bearing groups, through coupling chemistry after the peptide sequence is established. This strategy is particularly valuable when the probe architecture requires a specific residue position within a peptide context, while the final probe functionality is introduced at a later stage to match the requirements of the downstream assay or imaging/biophysical readout.
4. Pharmaceutical Intermediate Development
Boc-4-Iodo-L-Phenylalanine supports pharmaceutical intermediate development where iodinated aromatic amino acid residues are needed for late-stage diversification of peptide-like intermediates. Process and development chemists use this protected building block to prepare defined, stereochemically consistent intermediates that can be carried into coupling-based modification steps toward candidate structures. The combination of Boc protection for synthetic handling and the para-iodo substituent for downstream functionalization aligns with common industrial workflows for building complex, substituted aromatic motifs within peptide-derived scaffolds.
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