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Search for Fmoc-3-iodo-L-phenylalanine丨CAS 210282-31-8
Fmoc-3-Iodo-L-phenylalanine is a protected, halogenated amino acid derivative used in peptide synthesis and specialized organic chemistry. It features a 9-fluorenylmethoxycarbonyl (Fmoc) protecting group on the amino functionality and an iodine substituent at the meta position of the aromatic ring. The Fmoc group enables controlled amino-group deprotection in compatible synthetic workflows, while the aryl iodine provides a versatile site for further chemical modification. Its defined L-configuration makes this compound a useful building block for modified peptides, functionalized amino acids, and research intermediates.
Chemical Identifiers
| InChI | InChI=1S/C24H20INO4/c25-16-7-5-6-15(12-16)13-22(23(27)28)26-24(29)30-14-21-19-10-3-1-8-17(19)18-9-2-4-11-20(18)21/h1-12,21-22H,13-14H2,(H,26,29)(H,27,28)/t22-/m0/s1 |
| InChI Key | SSKOJXLIQFVOGC-QFIPXVFZSA-N |
| Smiles | C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CC4=CC(=CC=C4)I)C(=O)O |
| EC No. | 696-199-2 |
| MDL No. | MFCD01632252 |
| PubChem CID | 46737402 |
Applications
Applications in Peptide Synthesis
Fmoc-3-Iodo-L-phenylalanine can be incorporated into peptide sequences using suitable Fmoc-based solid-phase peptide synthesis methods. The Fmoc protecting group can be removed under compatible basic conditions to expose the amino group for subsequent coupling steps. Its L-configuration supports the preparation of peptides with defined stereochemistry, while the iodine-substituted aromatic side chain introduces an additional functional handle for further modification and peptide analogue development.
Applications in Medicinal Chemistry Research
Fmoc-3-Iodo-L-phenylalanine can support medicinal chemistry projects involving modified amino acids, peptide analogues, and functionalized compound libraries. The iodine substituent offers a potential route for further derivatization, while the Fmoc group facilitates its use in multistep synthesis. Researchers may use this building block to explore how aromatic substitution influences molecular properties, structural interactions, and biological activity.
Applications in Functionalized Amino Acid Development
This compound may serve as an intermediate in the preparation of specialized amino acid derivatives and functionalized peptide building blocks. The Fmoc protecting group supports controlled manipulation of the amino functionality, while the meta-positioned iodine provides a site for subsequent chemical transformations. Depending on the synthetic strategy, Fmoc-3-Iodo-L-phenylalanine can contribute to the development of modified peptides, research intermediates, and structurally diverse molecular libraries.
Applications in Cross-Coupling Chemistry
The carbon–iodine bond at the meta position of the aromatic ring can participate in suitable cross-coupling reactions, including palladium-catalyzed transformations. These reactions may enable the introduction of additional substituents and support the synthesis of structurally diverse L-phenylalanine derivatives. This functionality is useful for molecular diversification and synthetic route development, with reaction conditions selected according to the target structure and compatibility with the Fmoc protecting group.
