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Good Product Fmoc-D-3-Iodophenylalanine丨CAS 478183-67-4
Fmoc-D-3-Iodophenylalanine is a protected, halogenated derivative of D-phenylalanine used in peptide synthesis and advanced organic chemistry. It contains 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 D-configuration makes this compound a useful building block for modified peptides, functionalized amino acids, and specialized research molecules.
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-/m1/s1 |
| InChI Key | SSKOJXLIQFVOGC-JOCHJYFZSA-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. | 853-537-5 |
| MDL No. | MFCD03840402 |
| PubChem CID | 46737401 |
Applications
Applications in Peptide Synthesis
Fmoc-D-3-Iodophenylalanine can be used to introduce a D-configured, iodine-substituted aromatic residue into peptide sequences using suitable Fmoc-based synthesis methods. The Fmoc protecting group can be removed under compatible basic conditions, exposing the amino group for subsequent coupling steps. The D-configuration may influence peptide conformation and stability depending on the sequence, making this building block relevant to the development of modified peptides and peptide analogues.
Applications in Medicinal Chemistry Research
Fmoc-D-3-Iodophenylalanine can support medicinal chemistry research involving stereochemically defined amino acids, modified peptides, and functionalized molecular libraries. Its D-configuration offers an alternative to the corresponding L-amino acid, while the iodine substituent provides a potential route for further derivatization. Researchers can use this building block to investigate how stereochemistry and aromatic substitution influence molecular structure, physicochemical properties, and biological interactions.
Applications in Functionalized Amino Acid Development
This compound may serve as an intermediate for preparing specialized amino acid derivatives and functionalized peptide building blocks. The Fmoc protecting group supports controlled manipulation of the amino functionality, while the meta-iodinated aromatic ring provides a site for subsequent chemical transformations. Depending on the synthetic route, Fmoc-D-3-Iodophenylalanine can contribute to the preparation of modified peptides, compound libraries, and other research molecules.
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 preparation of structurally diverse D-phenylalanine derivatives. This functionality provides flexibility for synthetic route development and molecular diversification, with reaction conditions selected to suit the target structure and maintain compatibility with the Fmoc protecting group.
