Ac-p-iodo-D-Phe-OH is an N-acetyl-protected, para-iodinated D-phenylalanine derivative featuring a benzyl side chain bearing an iodine substituent at the para position. The molecule contains a terminal carboxylic acid (-COOH) and an N-acetylated amino group (-NH-COCH3), with stereochemistry specified as D at the α-carbon and the aromatic side chain providing a halogenated handle for further derivatization or coupling chemistry. It is used as a chemically defined amino acid building block or intermediate in peptide synthesis and structure-activity or labeling studies where the para-iodine substituent enables selective functionalization while the N-acetyl group modulates chemoselectivity during stepwise assembly of more complex amino acid and peptide derivatives.
CAT No: CP26711
CAS No:201351-59-9
Synonyms/Alias:AC-P-IODO-D-PHE-OH;201351-59-9;AC1OCUU5;Acetyl-4-iodo-D-phenylalanine;C11H12INO3;CTK4E3372;D-Phenylalanine,N-acetyl-4-iodo-;ZINC399561;6109AH;RT-011180;K-5889;(2R)-2-acetamido-3-(4-iodophenyl)propanoicacid
Ac-p-iodo-D-Phe-OH is an N-acetylated derivative of D-phenylalanine bearing a para-iodine substituent on the aromatic ring, providing a stable aryl iodide handle for downstream derivatization. The combination of D-stereochemistry and the aryl halide functionality makes this compound a practical building block for preparing radio/halogen-modified aromatic motifs and for constructing iodinated aromatic intermediates used in chemical biology and medicinal chemistry workflows. Its carboxylic acid functionality supports standard coupling and intermediate-manufacturing routes used in research-grade synthesis.
1. Iodinated Aromatic Intermediates
Ac-p-iodo-D-Phe-OH is used as a specialized iodinated aromatic intermediate for building aryl iodide-containing fragments in medicinal chemistry and SAR-oriented synthesis. Chemists commonly leverage the para-iodine substituent as a functional handle for subsequent cross-coupling or late-stage aromatic diversification, while the N-acetylated amino acid framework provides a defined stereochemical and functional context for assembling more complex structures. This grade of iodinated amino acid derivative is particularly useful when an iodinated phenylalanine motif is required as a precursor to analog libraries or as a component in multi-step synthesis where the aryl iodide must be introduced and retained in a controlled manner.
2. Peptide Fragment Building Block
Ac-p-iodo-D-Phe-OH is applied in the preparation of iodinated peptide fragments and peptide-like intermediates where an aryl iodide-substituted D-phenylalanine residue is desired. In custom peptide synthesis and peptide chemistry development, the N-acetylation state and the free carboxylic acid enable incorporation into defined coupling strategies to generate peptide segments that carry an aromatic iodide for later functionalization or analytical tagging. Researchers choose this derivative when they need the stereochemical rigidity associated with D-phenylalanine alongside a para-iodine substituent that can be carried through fragment assembly and then transformed at a later stage.
3. Chemical Biology Labeling Handles
Ac-p-iodo-D-Phe-OH is used as a chemical biology building block where an aryl iodide provides a convenient site for subsequent derivatization and probe construction. Molecular engineering teams often select iodinated aromatic amino acid derivatives to introduce a defined halogen-bearing aromatic functionality into larger constructs, including iodinated aromatic motifs within peptide-based probes or small-molecule tags. The N-acetylated amino acid scaffold helps maintain a consistent, reagent-like form for downstream assembly, while the para-iodine enables controlled introduction of new substituents or conjugation-compatible fragments in workflows that require a stable, well-defined aromatic handle.
4. Radiolabel and Halogenated Motif Prep
Ac-p-iodo-D-Phe-OH is leveraged in development workflows that require halogenated aromatic motifs as precursors to radio/iodine-containing analogs and iodinated reference compounds. Radiochemistry and tracer-development groups value aryl iodides as practical intermediates because they provide a direct entry point to iodinated aromatic structures that can be further processed into labeled targets or used as non-radioactive standards for method development. The D-phenylalanine backbone and N-acetylated form support reproducible intermediate preparation when stereochemistry and functional group placement are important for downstream synthesis, analytical characterization, or comparative studies using structurally matched iodinated materials.
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