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High Purity Boc-4-Iodo-L-phenylalanine丨CAS 62129-44-6
Boc-4-Iodo-L-phenylalanine is a protected, halogenated derivative of L-phenylalanine used in peptide chemistry and organic synthesis. It features a tert-butoxycarbonyl (Boc) protecting group on the amino group and an iodine substituent at the para position of the aromatic ring. The Boc group helps control the reactivity of the amino functionality during multistep synthesis, while the aryl iodine provides a versatile site for further chemical modification. These structural features make this compound useful for preparing functionalized amino acid derivatives, modified peptides, and specialized research molecules.
Chemical Identifiers
| InChI | InChI=1S/C14H18INO4/c1-14(2,3)20-13(19)16-11(12(17)18)8-9-4-6-10(15)7-5-9/h4-7,11H,8H2,1-3H3,(H,16,19)(H,17,18)/t11-/m0/s1 |
| InChI Key | JZLZDBGQWRBTHN-NSHDSACASA-N |
| Smiles | CC(C)(C)OC(=O)N[C@@H](CC1=CC=C(C=C1)I)C(=O)O |
| EC No. | 873-148-4 |
| MDL No. | MFCD00037119 |
| PubChem CID | 2755956 |
Applications
Applications in Peptide Synthesis
Boc-4-Iodo-L-phenylalanine can serve as a building block in peptide synthesis when a protected amino acid containing an aromatic iodine substituent is required. The Boc group supports selective protection strategies during peptide assembly and can be removed under suitable acidic conditions. Its L-configuration enables incorporation into target structures requiring the corresponding stereochemistry, while the iodine-bearing aromatic side chain introduces additional opportunities for subsequent functionalization.
Applications in Specialty Chemical Development
This compound may also be used in the synthesis of specialized amino acid derivatives and functionalized molecular libraries. By combining amino-group protection with an iodine-bearing aromatic ring, it offers two complementary points for synthetic planning: the Boc group can be managed during sequence construction, while the aryl iodine can be exploited for further derivatization. Its suitability for a particular application depends on the target molecule, reaction compatibility, and required purity.
Applications in Organic Synthesis and Functionalization
Applications in Chemical Biology Research
Halogenated amino acids are used in research to investigate how changes in amino acid side chains influence molecular structure, binding interactions, and biological activity. Boc-4-Iodo-L-phenylalanine can support the preparation of modified peptides and small molecules for structure–activity relationship studies. Its protected amino group and reactive aromatic substituent provide flexibility for researchers designing compounds with specific structural features.
