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Best Quality Boc-D-3-Iodophenylalanine丨CAS 478183-66-3
Boc-D-3-Iodophenylalanine is a protected, halogenated derivative of D-phenylalanine used in peptide chemistry and specialized organic synthesis. 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 D-configuration makes this compound a useful building block for 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-/m1/s1 |
| InChI Key | MPTBEGFNTNOLNZ-LLVKDONJSA-N |
| Smiles | CC(C)(C)OC(=O)N[C@H](CC1=CC(=CC=C1)I)C(=O)O |
| EC No. | |
| MDL No. | MFCD01860478 |
| PubChem CID | 46737391 |
Applications
Applications in Peptide Synthesis
Boc-D-3-Iodophenylalanine can be used in peptide synthesis strategies that employ Boc-protected amino acids. The protecting group can be removed under suitable acidic conditions to expose the amino group for subsequent coupling steps. Its D-configuration provides a stereochemical alternative to the corresponding L-amino acid, making it useful in the preparation of modified peptides and peptide analogues. The meta-iodinated aromatic side chain also offers opportunities for additional structural modification.
Applications in Medicinal Chemistry Research
Boc-D-3-Iodophenylalanine can support medicinal chemistry research involving modified amino acids, peptide-based compounds, and structure–activity relationship studies. The D-configuration may influence peptide conformation and stability depending on the sequence, while the iodine substituent provides a potential route for further functionalization. Researchers can use this building block to explore how stereochemistry and aromatic substitution affect molecular 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 molecular libraries. The Boc 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, Boc-D-3-Iodophenylalanine can contribute to the development of modified peptide building blocks and other research compounds.
Applications in Cross-Coupling Chemistry
The aryl carbon–iodine bond can participate in compatible cross-coupling reactions, including palladium-catalyzed transformations. These reactions may enable the introduction of new substituents at the meta position of the aromatic ring, supporting the synthesis of diverse D-phenylalanine derivatives. This functional handle is useful in synthetic route development and molecular diversification, with reaction conditions selected according to the target structure and compatibility with the Boc protecting group.
