Boc-4-Iodo-D-Phenylalanine is a Boc-protected, non-natural amino acid derivative featuring a D-phenylalanine backbone with an iodine substituent at the para (4-) position of the aromatic side chain. The molecule contains a Boc-protected amino group and a free carboxyl functional group, while the iodinated phenyl ring provides a heavy-atom handle that can influence reactivity and analytical detection. In peptide chemistry, this protected amino acid is used as a building block for incorporating an iodinated aromatic residue into peptide sequences via stepwise coupling strategies, and it also serves as a chemically defined precursor for preparing halogenated amino acid and peptide derivatives for labeling, conjugation, or structure-activity studies.
CAT No: CP15205
CAS No:176199-35-2
Synonyms/Alias:176199-35-2;Boc-4-iodo-D-phenylalanine;Boc-D-Phe(4-I)-OH;(R)-2-((tert-Butoxycarbonyl)amino)-3-(4-iodophenyl)propanoicacid;Boc-D-4-Iodophenylalanine;(2R)-2-[(tert-butoxycarbonyl)amino]-3-(4-iodophenyl)propanoicacid;C14H18INO4;AmbotzBAA1280;Boc-4-iodo-D-Phe;Boc-4'-iodo-D-Phe;AC1ODU6G;15044_ALDRICH;SCHEMBL3901262;(R)-2-(TERT-BUTOXYCARBONYLAMINO)-3-(4-IODOPHENYL)PROPANOICACID;15044_FLUKA;CTK7I3093;MolPort-001-758-541;ACT09133;ZINC2568077;9233AA;ANW-74347;CB-416;AKOS015836434;AM83378;RTR-008023
Boc-4-Iodo-D-Phenylalanine is a D-configured, non-proteinogenic amino acid derivative bearing a Boc-protected amino group and a para-iodo substituent on the aromatic side chain. This aryl iodide functionality makes it a practical electrophilic handle for downstream coupling chemistry, while the Boc protection supports its use as a protected amino acid building block in peptide and intermediate synthesis workflows. Researchers select this reagent when they need a stereochemically defined D-phenylalanine scaffold with a site-specific aryl functionalization point for medicinal chemistry, fragment elaboration, or protected-segment assembly.
1. Medicinal Chemistry Building Block
Boc-4-Iodo-D-Phenylalanine is commonly used in medicinal chemistry and peptidomimetic development as an aryl-iodide amino acid building block for late-stage diversification. The para-iodo group provides a convenient locus for C-C bond formation via palladium-catalyzed cross-coupling strategies, enabling rapid access to substituted aryl analogs while retaining the D-phenylalanine stereochemical element. Development teams often incorporate this scaffold into intermediate sequences that lead to kinase inhibitor fragments, receptor-binding motif analogs, or other aromatic pharmacophore variants where controlled substitution patterns are critical for structure-activity relationship studies.
2. Protected Segment For Peptide Synthesis
Boc-4-Iodo-D-Phenylalanine serves as a protected amino acid segment for solution-phase peptide synthesis and for preparing defined D-amino acid-containing intermediates. The Boc group supports controlled coupling chemistry in workflows where Boc-protected amino acids are assembled into peptide chains or used to generate peptide fragments for later joining. The para-iodo substituent allows researchers to introduce an additional functionalization step after peptide assembly planning, supporting strategies that require an aryl handle for subsequent derivatization without changing the stereochemical identity of the D-phenylalanine residue.
3. Cross-Coupling For Aromatic Diversification
Boc-4-Iodo-D-Phenylalanine is frequently selected as a chemically defined aryl iodide precursor for constructing substituted aromatic systems in pharmaceutical intermediate development. The C-I bond on the para position is well suited to iterative coupling chemistry, allowing substitution with aryl or heteroaryl partners to generate analog libraries with systematic electronic and steric variation. Because the amino acid backbone is protected, the reagent can be handled as a stable intermediate while transformation of the aromatic handle proceeds under conditions compatible with the protected amino functionality, supporting streamlined synthesis planning for research-scale library production.
4. Chiral Intermediate For SAR Studies
Boc-4-Iodo-D-Phenylalanine is used in stereochemically controlled intermediate synthesis when D-configuration is required for SAR exploration, conformational effects, or protease-stability design considerations in peptide-like scaffolds. The combination of D-phenylalanine stereochemistry and a para-iodo aromatic handle supports workflows where the same stereochemical core is carried through multiple derivatization routes to generate closely related analogs. Teams building structure-activity relationship series often rely on this type of protected, functionalized amino acid intermediate to maintain stereochemical consistency while varying the aromatic substitution pattern through downstream coupling chemistry.
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