DL-4-Iodophenylglycine is a non-proteinogenic, aromatic amino acid derivative featuring a phenylglycine backbone bearing an iodine substituent at the para (4-) position of the phenyl ring, with the amino acid framework containing both an amino group and a carboxyl group. The "DL" designation indicates a racemic mixture of stereoisomers at the alpha carbon, and the iodine-substituted aromatic side chain provides a heavy-atom handle that can participate in halogen-specific derivatization or labeling strategies while remaining compatible with amino acid coupling chemistry. DL-4-Iodophenylglycine is employed in peptide and amino acid derivative synthesis where an iodinated aromatic residue is incorporated for structure-activity studies, chemical biology probes, or analytical method development such as mass spectrometric detection and isotopic labeling workflows.
CAT No: CP10301
DL-4-Iodophenylglycine is a racemic (DL) phenylglycine derivative in which the side chain bears a para-position iodine substituent on the aromatic ring, providing a defined handle for halogen-influenced reactivity and downstream cross-coupling. The molecule contains the glycine backbone with both an amino functionality and a carboxylic acid group, enabling direct participation in amino acid coupling chemistry while maintaining the stereochemical context of a chiral center at the alpha carbon. The aryl iodide can undergo palladium-catalyzed transformations, and the amino and carboxyl groups can be protected or activated to support peptide bond formation and derivatization workflows. As an amino-acid-based intermediate, DL-4-Iodophenylglycine can be used to access iodinated aromatic motifs in peptidomimetics, SAR libraries, and synthetic organic routes where controlled incorporation of an aryl halide is required.
1. Peptide Synthesis
DL-4-Iodophenylglycine supports peptide building workflows through its amino acid functionality, where N-protection and C-activation strategies can be applied to form amide linkages under standard peptide coupling conditions. The carboxylic acid group can be converted into an activated ester or acid derivative compatible with coupling, while the amino group can be protected to suppress side reactions during chain assembly. The para-iodophenyl side chain remains available for later functionalization, allowing iodinated peptide fragments to be carried forward into analog synthesis or late-stage diversification. Racemic stereochemistry can be leveraged for generating mixed stereoisomer libraries when stereocontrol is not required, or it can serve as a starting point for downstream resolution or asymmetric incorporation strategies.
2. Chiral Building Blocks
DL-4-Iodophenylglycine is suitable as a chiral amino acid intermediate candidate because it contains an alpha stereocenter adjacent to the glycine backbone, even though the supplied material is racemic. The aryl iodide substituent provides an additional stereochemically informative functional group that can be retained during protection/deprotection sequences and used as a coupling partner in stereospecific or stereoretentive transformations after incorporation. Protecting-group strategies that temporarily mask the amino or carboxyl functionality can enable selective conversion of the molecule into N-protected amino acid derivatives, which can then be used in stereochemical studies or in the preparation of enantiomer-enriched analogs. The resulting iodinated chiral intermediate framework aligns with synthetic planning for amino acid derivatization and stereochemical SAR exploration.
3. Peptidomimetics And SAR
DL-4-Iodophenylglycine can be applied in peptidomimetic construction and structure-activity relationship studies where an iodinated aromatic side chain is used to probe binding-site tolerance and electronic effects. The amino acid backbone enables incorporation into scaffold-forming sequences via amide bond formation or conversion into constrained analogs, while the para-iodo substituent can be transformed into alternative aryl groups through cross-coupling to generate focused SAR panels. The presence of both amino and carboxyl functionalities allows conversion into protected intermediates for sequential synthesis, including routes that install additional substituents on the aromatic ring after scaffold assembly. Racemic stereochemistry supports rapid generation of stereochemical diversity for library synthesis, with subsequent identification of stereochemical preferences performed through downstream characterization and analog comparison.
4. Bioconjugation Chemistry
DL-4-Iodophenylglycine can serve as a biochemical research intermediate for constructing conjugatable amino acid motifs, particularly when an iodinated aromatic handle is desired for subsequent chemical modification. The alpha-amino and carboxyl groups allow transformation into protected amino acid derivatives that can be incorporated into peptide-like linkers or used to generate functionalized fragments for biomolecule labeling strategies. The aryl iodide can undergo substitution or coupling-based diversification to install reactive groups or affinity handles on a defined aromatic position, supporting modular linker design. The racemic starting material can be used to generate mixed stereoisomer conjugates for screening of labeling performance and stability, while protection-group compatibility supports controlled assembly of conjugation-ready intermediates.
5. Process Chemistry Intermediate
DL-4-Iodophenylglycine is relevant to process chemistry and fine chemical synthesis as an iodinated amino acid intermediate where halogen retention and controlled functional-group interconversion are important for manufacturing routes. The aryl iodide can be carried through protection and activation steps for peptide coupling or scaffold assembly, then converted in later stages to meet target specification for downstream intermediates. The amino acid's bifunctional nature enables straightforward conversion into N-protected and/or activated forms, supporting scalable synthesis planning that minimizes side reactions from free amino or carboxyl groups. The compound's structural features make it applicable to industrial intermediate preparation for iodinated aromatic fragments used in specialized chemical production, including downstream library manufacturing and chemical manufacturing workflows that require an aryl iodide-bearing stereochemical building block.
2. Store-operated Ca2+ entry sustains the fertilization Ca2+ signal in pig eggs
3. Immune-awakening Saccharomyces-inspired nanocarrier for oral target delivery to lymph and tumors
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