2-Iodo-DL-Phenylalanine is an iodinated, non-proteinogenic amino acid derivative in which the phenylalanine scaffold bears an iodine substituent at the 2-position of the alpha-carbon framework, and the "DL" designation indicates a racemic mixture of stereoisomers. The molecule contains both an amino group and a carboxyl group characteristic of amino acid building blocks, while the side chain remains a benzyl-linked aromatic functionality that can participate in hydrophobic and aromatic interactions in peptide contexts. As a halogenated phenylalanine analogue, it is used as a substrate or incorporation component in peptide synthesis and structure-activity or labeling studies, where the iodine atom provides a convenient chemical handle for analytical detection and for designing halogen-dependent physicochemical properties.
CAT No: CP15003
2-Iodo-DL-Phenylalanine is an iodinated phenylalanine derivative provided as a DL mixture, featuring a halogenated aromatic ring substitution at the ortho position relative to the amino acid side chain. The presence of the iodine atom makes this building block useful for radio- and mass-sensitive labeling strategies, while the amino acid functionality supports downstream conversion into peptide fragments and analytical reference materials. Researchers select this compound when an ortho-iodinated aromatic handle is required for incorporation into synthetic sequences or for quantification workflows where distinctive mass and isotope/halogen signatures improve traceability.
1. Peptide Fragment Building
2-Iodo-DL-Phenylalanine is used as an amino acid building block for preparing iodinated peptide fragments and peptidomimetic structures in medicinal chemistry and chemical biology programs. Synthetic teams commonly incorporate this ortho-iodinated aromatic residue to introduce a defined halogenated side chain into sequence-relevant scaffolds, enabling subsequent derivatization or use as a structural probe within larger peptide assemblies. The DL stereochemical form supports broader library-style synthesis where stereochemical uniformity is not the primary requirement, such as exploratory SAR studies and intermediate generation for later stereochemical refinement.
2. Radiolabeling and Tracer Studies
2-Iodo-DL-Phenylalanine is selected in tracer-oriented workflows where the iodine-containing aromatic motif provides a convenient platform for labeling strategies and downstream detection. Research groups use iodinated amino acid derivatives to generate distinct analytical signals for tracking incorporation into synthetic constructs or for method development in isotope-aware analytical measurements. The ortho-iodine substitution offers a stable, chemically addressable feature that can be leveraged to create measurable mass shifts or iodine-specific signatures, supporting quantitative studies that require clear differentiation from unlabeled analogs.
3. Analytical Standards and LC-MS Quantification
2-Iodo-DL-Phenylalanine is widely used to prepare analytical standards for LC-MS method development, calibration, and confirmation of iodinated aromatic amino acid derivatives in complex mixtures. Analytical chemists value the distinctive iodine mass contribution and the defined amino acid backbone for building retention-time and fragmentation reference sets, particularly when monitoring iodinated species in synthetic reaction monitoring, impurity profiling, or stability/compatibility studies of iodinated intermediates. Using the DL material as a standard also supports workflows where total (racemic) levels are measured rather than enantiomer-resolved quantitation.
4. Pharmaceutical Intermediate Development
2-Iodo-DL-Phenylalanine serves as a practical intermediate for manufacturing iodinated aromatic building blocks used in downstream medicinal chemistry synthesis. Process development teams and specialty chemical manufacturers employ this compound to access ortho-iodinated phenylalanine-derived motifs that can be further transformed into substituted aromatic intermediates, coupling partners, or protected amino acid derivatives for custom synthesis. The amino acid functionality provides a convenient entry point into protected/activated derivatives during intermediate manufacturing, while the iodine substituent remains a key structural feature for later C-C or C-heteroatom bond-forming steps in synthetic pipelines.
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