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High Purity Boc-L-3-Iodophenylalanine丨CAS 273221-75-3
Boc-L-3-Iodophenylalanine is a protected, halogenated derivative of L-phenylalanine used in peptide synthesis and specialized organic chemistry. It features a tert-butoxycarbonyl (Boc) protecting group on the amino functionality and an iodine substituent at the meta position of the aromatic ring. The Boc group helps control amino-group reactivity during multistep synthesis, while the aryl iodine provides a versatile site for further chemical modification. Its defined L-configuration makes this compound useful for preparing stereochemically specific amino acid derivatives, modified peptides, and functionalized research molecules.
Chemical Identifiers
| InChI | InChI=1S/C14H18INO4/c1-14(2,3)20-13(19)16-11(12(17)18)8-9-5-4-6-10(15)7-9/h4-7,11H,8H2,1-3H3,(H,16,19)(H,17,18)/t11-/m0/s1 |
| InChI Key | MPTBEGFNTNOLNZ-NSHDSACASA-N |
| Smiles | CC(C)(C)OC(=O)N[C@@H](CC1=CC(=CC=C1)I)C(=O)O |
| EC No. | 853-537-5 |
| MDL No. | MFCD01860644 |
| PubChem CID | 11728885 |
Applications
Applications in Peptide Synthesis
Boc-L-3-Iodophenylalanine can serve as a building block in peptide synthesis strategies that use Boc-protected amino acids. The Boc group can be removed under suitable acidic conditions to expose the amino group for subsequent coupling steps, supporting controlled peptide assembly. Its L-configuration is useful when a defined stereochemical structure is required, while the meta-iodinated aromatic side chain provides additional opportunities for modification in peptide and amino acid research.
Applications in Medicinal Chemistry Research
Boc-L-3-Iodophenylalanine can support medicinal chemistry research involving modified amino acids, peptide analogues, and functionalized compound libraries. The iodine substituent offers a potential site for further derivatization, while the Boc group facilitates controlled manipulation of the amino functionality during synthesis. Researchers may use this building block to explore how aromatic substitution affects molecular structure, physicochemical properties, and biological interactions.
Applications in Functionalized Amino Acid Development
This compound may be used as an intermediate in the preparation of specialized amino acid derivatives and functionalized peptide building blocks. The Boc protecting group supports selective transformations involving the amino functionality, while the meta-positioned iodine provides an opportunity for subsequent chemical modification. Depending on the synthetic strategy, Boc-L-3-Iodophenylalanine can contribute to the development of modified peptides, research intermediates, and structurally diverse molecular libraries.
Applications in Cross-Coupling Chemistry
The aryl carbon–iodine bond can participate in compatible cross-coupling reactions, including palladium-catalyzed transformations. These reactions may allow the introduction of additional substituents at the meta position of the aromatic ring, enabling the preparation of diverse phenylalanine derivatives. This functional handle can support molecular diversification and synthetic route development, with reaction conditions selected according to the target structure and compatibility with the Boc protecting group.
