2-Iodo-L-Phenylalanine is an iodinated aromatic amino acid derivative in which an iodine atom is substituted at the 2-position of the phenylalanine side-chain ring relative to the α-amino acid backbone, retaining the α-amino and α-carboxyl functional groups. The molecule bears an L-stereochemical configuration as indicated by the name and features a benzyl-like side chain with a halogenated aromatic substitution, while the iodine substituent provides a distinct mass and polarizability handle for chemical labeling and spectroscopic detection. In research workflows, this compound is used as a halogenated amino acid building block for peptide and protein structure-activity studies, as a substrate for analytical method development involving isotope/elemental signatures, and as a precursor for further derivatization of the aromatic ring in synthetic chemistry.
CAT No: CP15001
CAS No:167817-55-2
Synonyms/Alias:2-Iodo-l-phenylalanine;167817-55-2;(S)-2-Amino-3-(2-iodophenyl)propanoicacid;Phenylalanine,2-iodo-;(2S)-2-AMINO-3-(2-IODOPHENYL)PROPANOICACID;L-Phe(2-I)-OH;SCHEMBL158930;CTK0H1709;BKXVGLPBXYBDDM-QMMMGPOBSA-N;MolPort-020-004-165;ZINC2385606;ANW-22310;AKOS015907891;AM83359;AJ-35164;AK-60882;AM009284;KB-24678;TC-111055;V3702;I14-25452
2-Iodo-L-Phenylalanine is an iodinated, proteinogenic amino acid building block featuring an L-configuration and a reactive aromatic side chain bearing iodine at the ortho (2-) position. This halogenated phenylalanine is widely used in chemical biology and peptide chemistry workflows where an iodine-substituted aromatic residue provides a convenient handle for radiolabeling, halogen-based derivatization, and site-specific incorporation into peptides. Its defined stereochemistry and aromatic functionality make it a practical precursor for constructing labeled biomolecular probes and for preparing analytical standards that distinguish ortho-iodinated phenylalanine motifs.
1. Radiolabeling And Tracers
2-Iodo-L-Phenylalanine is used as a precursor for developing iodine-based tracers and radiolabeled analogs in research settings that require controlled introduction of an ortho-iodinated aromatic residue. Teams in tracer chemistry and chemical biology commonly select this building block to enable site-specific labeling strategies where the iodinated phenylalanine motif is incorporated into peptides or used as a reference material for downstream radiochemical workflows and method development. The presence of a single iodine substituent on the aromatic ring supports straightforward tracking by iodine-sensitive analytical techniques and supports workflows where the label must be positioned on the phenyl ring rather than elsewhere in the molecule.
2. Peptide Synthesis Building Block
2-Iodo-L-Phenylalanine is incorporated into peptides during peptide synthesis to introduce an ortho-iodinated phenylalanine residue for structural studies, binding studies, and labeling-compatible peptide design. Peptide chemists and medicinal chemistry groups use this amino acid to generate peptide libraries and defined peptide standards where the iodinated aromatic side chain serves as a chemically addressable feature for later derivatization or analytical readout. Because it is an L-amino acid with a native-like amino acid backbone, it integrates into established peptide assembly workflows used for site-specific residue placement, enabling reproducible construction of peptides that contain the 2-iodophenylalanine motif.
3. Chemical Biology Probe Development
2-Iodo-L-Phenylalanine supports probe construction in chemical biology projects that require an iodine-bearing aromatic handle for labeling, derivatization, or analytical tagging of biomolecular targets. Researchers developing mechanistic probes and structure-activity relationship tools often choose ortho-iodinated phenylalanine to create defined, residue-level probes that can be tracked by iodine-aware detection methods or further functionalized after incorporation into a peptide or small molecule scaffold. This makes the reagent useful for workflows that prioritize positional control of the aromatic iodine substituent, especially when comparing probe variants that differ specifically at the iodinated phenylalanine position.
4. Analytical Standards For LC-MS
2-Iodo-L-Phenylalanine is used to prepare analytical standards and reference materials for quantitative and qualitative mass spectrometry workflows that need an authentic ortho-iodinated phenylalanine species. Analytical chemistry groups use this compound to calibrate instruments, validate chromatographic separation of iodinated amino acid motifs, and support identification of iodinated fragments or peptide components containing the 2-iodophenylalanine residue. The defined structure and stereochemistry help reduce ambiguity in spectral interpretation for studies involving iodinated amino acid derivatives, iodinated peptide standards, or method development where iodine-containing aromatic analytes must be reliably distinguished from non-iodinated analogs.
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