Hangzhou Leap Chem Co., Ltd. is one of the most professional manufacturers and suppliers of fmoc-d-2-iodophenylalanine丨cas 478183-65-2 in China. Welcome to wholesale bulk high quality chemical products at competitive price from our factory. If you have any enquiry about custom service, please feel free to email us.
Bulk Supply Fmoc-D-2-Iodophenylalanine丨CAS 478183-65-2
Fmoc-D-2-Iodophenylalanine is a protected, halogenated derivative of D-phenylalanine 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 ortho position of the aromatic ring. The Fmoc group enables controlled amino-group deprotection in compatible synthesis workflows, while the aryl iodine provides a versatile site for further chemical modification. Its defined D-configuration makes this compound valuable for preparing stereochemically specific amino acid derivatives, modified peptides, and functionalized research molecules.
Chemical Identifiers
| InChI | InChI=1S/C24H20INO4/c25-21-12-6-1-7-15(21)13-22(23(27)28)26-24(29)30-14-20-18-10-4-2-8-16(18)17-9-3-5-11-19(17)20/h1-12,20,22H,13-14H2,(H,26,29)(H,27,28)/t22-/m1/s1 |
| InChI Key | YMKDZEDXFIXGNK-JOCHJYFZSA-N |
| Smiles | C1=CC=C(C(=C1)C[C@H](C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)I |
| EC No. | |
| MDL No. | MFCD06796745 |
| PubChem CID | 56777136 |
Applications
Applications in Peptide Synthesis
Fmoc-D-2-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 basic conditions compatible with the selected synthesis strategy, allowing subsequent amino acid coupling. The D-configuration may influence peptide conformation and stability depending on the sequence, making this building block relevant to research on modified peptides and peptide analogues.
Applications in Medicinal Chemistry Research
Fmoc-D-2-Iodophenylalanine supports 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 molecular diversification. Researchers can use this building block to investigate how stereochemistry and aromatic substitution affect molecular conformation, physicochemical properties, and biological interactions.
Applications in Functionalized Amino Acid Development
This compound can also serve as an intermediate in the development of specialized amino acid derivatives and research compounds. The Fmoc group supports controlled manipulation of the amino functionality, while the aryl iodine offers a site for subsequent chemical transformations. Depending on the synthetic route, Fmoc-D-2-Iodophenylalanine may contribute to the preparation of modified peptide building blocks and structurally diverse amino acid libraries.
Applications in Cross-Coupling Chemistry
The carbon–iodine bond at the ortho 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 the preparation of structurally diverse D-phenylalanine derivatives. The ortho position can create a distinct steric environment that influences reaction behavior, so the choice of catalyst and conditions should account for the target structure and compatibility with the Fmoc protecting group.
