L-4-Iodophenylglycine is an L-configured, non-proteinogenic aromatic amino acid derivative featuring a phenylglycine backbone bearing a para-iodo substituent on the aromatic ring. The molecule contains a primary amino group and a carboxyl group characteristic of amino acids, with the side chain presenting an iodinated aryl functionality that can participate in halogen-dependent chemical reactivity and serves as a handle for labeling or cross-coupling-style transformations. In peptide and chemical biology research, it is used as a substituted phenylglycine building block for structure-activity studies, incorporation into synthetic peptide analogues, and analytical or conjugation workflows where an iodinated aromatic moiety provides a defined chemical tag.
CAT No: CP10302
L-4-Iodophenylglycine is an L-configured amino acid derivative in which the glycine backbone is substituted with a para-iodophenyl side chain, creating a chiral amino acid intermediate with a stereogenic center at the alpha carbon. The molecule contains a primary amino group and a carboxylic acid (or can be handled as a protected/activated form), while the aryl iodide provides a distinct electrophilic handle for cross-coupling and late-stage functionalization. The para-iodo substituent strongly influences aromatic reactivity and enables selective derivatization without disturbing the amino acid functionality. The combination of amino acid stereochemistry and a programmable aryl halide makes L-4-Iodophenylglycine a practical precursor for peptide-compatible building blocks and downstream synthetic intermediates in amino acid chemistry.
1. Peptide Synthesis
L-4-Iodophenylglycine is used in peptide building block preparation where the L-amino acid stereocenter supports stereochemically defined incorporation into peptide chains. The aryl iodide on the side chain can be preserved through standard N- and C-terminal protection strategies, allowing peptide coupling chemistry to proceed while retaining a functional handle for post-coupling diversification. The amino and carboxyl functionalities enable formation of amide bonds via conventional protected amino acid activation, and the aromatic ring can participate in side-chain-directed structure studies after peptide assembly. L-4-Iodophenylglycine can therefore serve as a precursor to iodinated peptide analogs and peptide fragments used for mapping binding motifs and generating halogenated peptidomimetic scaffolds.
2. Chiral Cross-Coupling Intermediate
L-4-Iodophenylglycine supports chiral synthetic organic chemistry because the L-configuration at the alpha carbon is retained while the para-iodophenyl group undergoes palladium-catalyzed or related halide-to-functionality transformations. The aryl iodide enables conversion to arylboronates, arylated motifs, or other substituted aromatic derivatives that can tune electronic properties and molecular recognition features while leaving the amino acid core available for further derivatization. Protection of the amino and carboxyl groups can be applied to control chemoselectivity during coupling steps, producing stereodefined chiral intermediates for medicinal chemistry and process-scale fine chemical synthesis. Downstream, functionalized aromatic amino acid derivatives derived from L-4-Iodophenylglycine can be used to construct diversified libraries for structure-activity relationship studies and fragment-based scaffold elaboration.
3. Chemical Biology Labeling
L-4-Iodophenylglycine can be applied in chemical biology workflows requiring amino acid-based probes that combine a defined stereocenter with an aryl iodide for modular tag installation. The amino acid functionality allows incorporation into peptides or conjugation-ready derivatives, while the para-iodophenyl group can be transformed into bioorthogonal or affinity-bearing aromatic substituents through controlled derivatization strategies. The resulting iodinated or substituted aromatic amino acid motifs can be used to generate labeled biomolecule fragments for receptor-binding studies, proteomic reagent development, or targeted chemical mapping. L-4-Iodophenylglycine thus functions as a stereochemically defined intermediate enabling downstream probe construction and biomolecule modification chemistry.
4. SAR Studies And Molecular Design
L-4-Iodophenylglycine is suitable for structure-activity relationship studies and molecular design efforts where para-substituted aromatic amino acids help probe how aryl electronics and steric effects influence target interactions. The intact amino acid backbone allows systematic variation of side-chain substitution patterns while maintaining the L-amino acid geometry that governs peptide conformation and recognition. The aryl iodide provides a direct synthetic entry to substituted phenyl analogs, enabling rapid generation of analog series for SAR experiments and combinatorial library synthesis. L-4-Iodophenylglycine can therefore serve as a chiral platform intermediate for designing peptidomimetics and aromatic amino acid derivatives with controlled stereochemical identity.
5. Pharmaceutical Intermediate Preparation
L-4-Iodophenylglycine is relevant to pharmaceutical intermediate preparation because it combines an amino acid handle compatible with protected amino acid chemistry and an aryl iodide suitable for manufacturing-friendly diversification routes. The presence of a stereogenic alpha carbon supports the synthesis of enantiopure aromatic amino acid motifs that can be carried into peptide-like intermediates, enzyme-binding fragments, or heteroaryl-substituted analogs through sequential protection, coupling, and functional group transformations. The carboxylic acid and amino group enable conversion to activated derivatives (e.g., ester or protected amine forms) for controlled downstream assembly in fine chemical manufacturing. L-4-Iodophenylglycine can be employed as a chiral intermediate for producing iodinated and subsequently functionalized amino acid derivatives used in industrial-scale synthetic planning.
6. Analytical Standards Development
L-4-Iodophenylglycine can be utilized in analytical research as a stereochemically defined reference material for method development involving amino acid derivatization, chiral analysis, or LC-MS characterization of iodinated aromatic amino acid species. The para-iodophenyl group provides a strong mass spectrometric signature and can improve detectability relative to non-halogenated analogs, supporting quantitation and impurity profiling in synthetic intermediate streams. The amino acid functional groups allow conversion into stable derivatives for chromatographic behavior tuning, including protected forms used to validate peptide coupling-related workflows. L-4-Iodophenylglycine therefore serves as a practical analytical anchor for monitoring protected amino acid synthesis, side-chain functionalization, and downstream transformation products in amino acid chemistry pipelines.
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