4-Iodo-D-Phenylalanine is a D-configured phenylalanine derivative in which the para position of the benzyl side chain is substituted with an iodine atom, yielding an aromatic, halogenated amino acid suitable for chemical probing and labeling. The molecule contains a free amino group and a free carboxyl group on the α-carbon, and the iodinated aryl side chain provides a distinct mass and polarizability while remaining compatible with amino acid handling in peptide and conjugation workflows. In research contexts, it is used as a building block for preparing iodinated peptides and for incorporating a spectroscopic or mass-tag handle into amino-acid-derived structures for analytical method development, structure-activity studies, and molecular labeling.
CAT No: CP15202
CAS No:62561-75-5
Synonyms/Alias:4-Bromo-D-phenylalanine;62561-74-4;d-4-Bromophenylalanine;(r)-2-amino-3-(4-bromophenyl)propanoicacid;H-D-Phe(4-Br)-OH;(2R)-2-amino-3-(4-bromophenyl)propanoicacid;4-Bromo-D-Phe-OH;D-4-Br-Phe-OH;H-P-BROMO-D-PHE-OH;D-PHE(4-BR)-OH;(R)-2-AMINO-3-(4'-BROMOPHENYL)PROPANOICACID;(s)-2-amino-3-(4'-bromophenyl)propanoicacid;D-4-Bromophe;AC1LDOOF;PubChem18011;PubChem18012;AC1Q4UAQ;KSC493O6L;SCHEMBL244718;P-BROMO-D-PHENYLALANINE;CTK3J3765;ZINC32334;MolPort-001-758-737;ANW-53165;CB-510
4-Iodo-D-Phenylalanine is a D-configured phenylalanine analog bearing an iodo substituent on the aromatic ring, providing a heavy-atom handle that is widely used in chemical biology and medicinal chemistry workflows. Its stereochemical definition and aromatic iodination make it a practical building block for preparing halogenated amino acid derivatives, radiolabeling precursors, and site-specific probes where controlled aromatic substitution is required. Researchers also use this compound as a defined chiral amino acid starting material for downstream synthesis of iodinated peptidomimetics and structure-activity relationship (SAR) analogs.
1. Medicinal Chemistry SAR Building Blocks
4-Iodo-D-Phenylalanine is used by medicinal chemistry groups to generate iodinated analogs for structure-activity relationship studies in peptidomimetic and small-molecule programs. The aromatic iodine provides a convenient physicochemical "modulation point" for tuning sterics and electronic properties while maintaining the amino acid backbone geometry associated with D-phenylalanine derivatives. In practice, it is commonly incorporated into synthetic routes that produce defined halogenated intermediates for library synthesis, allowing chemists to compare analog series where the iodine position and stereochemical configuration are controlled.
2. Peptidomimetic And Modified Peptides
4-Iodo-D-Phenylalanine serves as a chiral amino acid building block for preparing D-phenylalanine-containing peptidomimetics and modified peptide scaffolds. The iodinated aromatic ring supports the construction of analogs used in protease/peptidomimetic stability studies and conformation-focused design, where maintaining a specific stereochemical identity is important for interpreting structure-property trends. Teams performing custom peptide synthesis and peptide-analog development also value the defined aromatic substitution for generating consistent, analytically trackable variants across series.
3. Radiolabeling And Heavy-Atom Labeling
4-Iodo-D-Phenylalanine is frequently selected as a precursor for iodine-based labeling strategies in chemical biology and analytical development. The presence of an aryl iodide enables downstream incorporation of iodine into labeled derivatives, supporting workflows that require a heavy-atom tag for imaging-related chemistry or for creating defined iodinated standards used in method development. Because the labeling handle is embedded on the aromatic ring of a stereochemically defined amino acid, it is particularly useful when researchers need to preserve the chiral amino acid identity while introducing an iodine label for subsequent detection or analytical tracking.
4. Chemical Biology Probe Precursors
4-Iodo-D-Phenylalanine is used to build probe precursors where an iodinated aromatic motif is advantageous for downstream derivatization and characterization. Chemical biology teams often leverage this compound to prepare site-defined aromatic substitutions that can be carried through to probe candidates, including iodinated intermediates that later undergo functional group transformations to install additional reporter or binding elements. The combination of a D-amino acid stereocenter with an aryl iodide handle helps maintain structural fidelity between precursor and final probe, which is important for correlating analytical data with probe structure.
2. High fat diet and GLP-1 drugs induce pancreatic injury in mice
5. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at . We will endeavor to provide highly satisfying products and services.
Creative Peptides is a trusted CDMO partner specializing in high-quality peptide synthesis, conjugation, and manufacturing under strict cGMP compliance. With advanced technology platforms and a team of experienced scientists, we deliver tailored peptide solutions to support drug discovery, clinical development, and cosmetic innovation worldwide.
From custom peptide synthesis to complex peptide-drug conjugates, we provide flexible, end-to-end services designed to accelerate timelines and ensure regulatory excellence. Our commitment to quality, reliability, and innovation has made us a preferred partner across the pharmaceutical, biotechnology, and personal care industries.
Read More