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Order L-4-Iodophenylalanine丨CAS 24250-85-9
L-4-Iodophenylalanine is a halogenated derivative of L-phenylalanine featuring an iodine substituent at the para position of the aromatic ring. This non-standard amino acid combines the defined L-configuration of phenylalanine with a reactive aryl iodide group, making it a valuable building block for organic synthesis, medicinal chemistry, and peptide research. The iodine substituent can serve as a versatile functional handle for further chemical transformations, enabling the development of structurally diverse amino acid derivatives and research compounds.
Chemical Identifiers
| InChI | InChI=1S/C9H10INO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m0/s1 |
| InChI Key | PZNQZSRPDOEBMS-QMMMGPOBSA-N |
| Smiles | C1=CC(=CC=C1C[C@@H](C(=O)O)N)I |
| EC No. | 849-052-3 |
| MDL No. | MFCD00002602 |
| PubChem CID | 134497 |
Applications
Applications in Peptide Synthesis
As a non-proteinogenic amino acid, L-4-Iodophenylalanine may be incorporated into selected peptide synthesis workflows when a modified aromatic side chain is desired. Its L-configuration supports the preparation of stereochemically defined peptides, while the iodine substituent introduces additional possibilities for side-chain modification. Depending on the synthesis strategy, suitable protection and coupling methods may be required to achieve the intended peptide structure.
Applications in Medicinal Chemistry
L-4-Iodophenylalanine can be used as a specialized intermediate in medicinal chemistry research and the synthesis of amino-acid-derived compounds. The para-iodinated aromatic ring provides opportunities for further functionalization, supporting the preparation of molecular analogues and the investigation of structure–activity relationships. Its defined L-stereochemistry is particularly relevant when the spatial arrangement of the amino acid is important to the target molecular structure.
Applications in Organic Synthesis and Functionalization
Applications in Chemical Biology Research
L-4-Iodophenylalanine can support chemical biology research involving modified amino acids, functionalized peptides, and molecular interaction studies. The iodine substituent offers a potential site for chemical elaboration, while the amino acid framework provides a recognizable structural scaffold for molecular design. Its suitability for a specific biological or analytical application depends on the target system and the selected experimental methodology.
