D-4-Iodophenylglycine is a D-configured, non-proteinogenic amino acid derivative featuring a glycine backbone bearing a para-iodophenyl side chain, classifiable as an aryl-substituted amino acid. The molecule contains a primary amino group and a carboxylic acid functionality, with the aromatic ring bearing an iodine substituent that provides a distinct mass and a chemically addressable handle for labeling or derivatization. D-4-Iodophenylglycine is used in peptide and protein structure-activity studies, where the aryl iodide can support incorporation into synthetic analogs and facilitate analytical tracking or subsequent chemical modification.
CAT No: CP10303
D-4-Iodophenylglycine is a D-configured amino acid derivative in which the stereogenic center on the glycine backbone bears a 4-iodophenyl substituent, providing a chiral, aryl-functionalized building block for stereoselective synthesis. The molecule contains a carboxylic acid and a primary amine that can be differentially protected to control chemoselectivity during peptide coupling and subsequent functional group transformations. The para-iodo substituent serves as a high-leaving-point handle for cross-coupling chemistry, enabling conversion into aryl halide-derived motifs while preserving the amino acid stereochemistry. The combination of amino acid reactivity and aryl iodide functionality makes D-4-Iodophenylglycine a practical intermediate for chiral scaffold elaboration, peptide analog construction, and downstream medicinal chemistry-style diversification.
1. Peptide Synthesis
D-4-Iodophenylglycine is applied in peptide synthesis as a chiral phenylglycine residue whose D-configuration can be retained through standard N- and C-terminal protection strategies. The carboxylic acid and amine functional groups can be orthogonally protected to enable amide bond formation while minimizing side reactions from the aryl iodide under coupling conditions. The 4-iodophenyl side chain can be incorporated into peptide backbones to generate aryl-bearing peptide fragments suitable for later aryl functionalization, including cross-coupling-driven diversification of peptide analogs. Peptide building block incorporation supports structure-activity relationship studies where stereochemistry and aromatic substitution patterns are varied systematically.
2. Chiral Synthesis Intermediate
D-4-Iodophenylglycine functions as a chiral amino acid intermediate for stereoselective construction of aryl-substituted frameworks in synthetic organic chemistry. The D-stereocenter provides a defined spatial arrangement of the amino acid backbone relative to the para-iodophenyl group, supporting downstream transformations that preserve stereochemical integrity. The iodide substituent enables sequential derivatization through C-C bond-forming reactions, allowing access to substituted phenylglycine derivatives without changing the amino acid core. Chiral intermediate use extends to fragment elaboration for peptidomimetics and non-peptidic scaffolds derived from amino acid-derived stereocenters.
3. Cross-Coupling Diversification
D-4-Iodophenylglycine is utilized in chemical manufacturing and fine chemical synthesis as an aryl iodide-bearing amino acid platform for diversification via palladium-catalyzed cross-coupling chemistry. The para-iodo group can be converted into aryl-alkenyl or aryl-aryl linkages, supporting generation of substituted phenylglycine derivatives that retain the amino acid functionality for further derivatization. The presence of both carboxylic acid and protected amine enables retention of a handle for subsequent peptide coupling or conversion into activated derivatives for downstream synthesis. Cross-coupling-driven diversification supports scalable preparation of intermediate libraries used in industrial process chemistry and specialty chemical production.
4. Peptidomimetics And SAR
D-4-Iodophenylglycine supports peptidomimetic construction in drug discovery research by providing a stereodefined, aromatic side-chain amino acid analog for backbone mimicry. The D-phenylglycine motif enables incorporation into constrained peptide-like structures where aromatic substitution and stereochemistry influence conformational preferences and binding-site interactions. The amino acid functional groups can be protected to allow sequential assembly of analogs, while the para-iodophenyl moiety can be transformed to tune electronic and steric properties during SAR studies. Downstream use includes generating aryl-substituted peptide analogs and non-natural amino acid-containing scaffolds suitable for iterative medicinal chemistry-style evaluation.
5. Biomolecule Labeling
D-4-Iodophenylglycine can be applied in chemical biology for biomolecule labeling and biomolecule modification workflows that require a chiral, aromatic amino acid handle. The amino acid backbone enables conversion into activated derivatives or protected forms for conjugation strategies, while the 4-iodophenyl group can be used as a functional handle for subsequent coupling to introduce reporter-compatible aryl substituents. The D-configuration helps maintain stereochemical fidelity when the residue is incorporated into peptide tags, protein fragments, or labeled ligands. Labeling-oriented use supports preparation of chiral, aryl-functional conjugates that can be further processed into analytical standards or molecular probes.
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