Fmoc-2-Iodo-D-Phenylalanine is a protected, non-natural amino acid derivative featuring a phenylalanine backbone bearing an iodine substituent at the 2-position of the side chain and the D stereochemical configuration at the α-carbon as indicated by the product name. The molecule contains a free carboxyl group and an N-terminus protected by the Fmoc group, while the aromatic side chain provides a hydrophobic aryl functionality and the iodo substituent serves as a halogenated handle for subsequent chemical transformations. In peptide chemistry and chemical biology workflows, it is employed as a stepwise building block for incorporating a halogenated phenylalanine analogue into protected peptide intermediates and for preparing labeled or structure-activity study peptides where the aryl iodide can be used for downstream conjugation or derivatization strategies.
CAT No: CP15007
Fmoc-2-Iodo-D-Phenylalanine is an Fmoc-protected D-phenylalanine derivative bearing an ortho-iodine substituent on the aromatic ring, providing a stereodefined chiral amino acid building block for peptide chemistry. The molecule contains a fluorenylmethoxycarbonyl (Fmoc) group on the amino functionality and a carboxyl functionality masked as an unreactive form suitable for standard peptide coupling workflows, while the aryl iodide serves as a reactive handle for cross-coupling and late-stage functionalization. The D-configuration at the alpha carbon controls stereochemical outcomes in peptide assembly and in downstream structure-property studies, while the ortho-iodine can influence conformational preferences and electronic effects on the phenyl side chain. The combination of a protected amino acid scaffold and a carbon-iodine bond makes the compound a practical intermediate for constructing aryl-substituted peptides and for preparing radiolabelable or derivatizable aromatic motifs.
1. Peptide Synthesis
Fmoc-2-Iodo-D-Phenylalanine is applied in peptide building workflows where Fmoc removal and subsequent amide bond formation require a stable, orthogonally protected amino acid. The Fmoc-protected amino group and the chiral D-phenylalanine backbone support routine peptide coupling chemistry, enabling incorporation of an aryl-iodinated residue into peptide sequences for SAR studies and peptide analog generation. The ortho-iodine substituent functions as a latent functional group that can be retained through assembly and later converted via palladium-catalyzed cross-coupling to diversify side-chain electronics and sterics. The resulting iodinated peptides can serve as intermediates for further derivatization, purification development, and library synthesis in peptide science and synthetic organic chemistry.
2. Side-Chain Functionalization
Fmoc-2-Iodo-D-Phenylalanine is used for side-chain functionalization strategies that exploit the aryl iodide as a cross-coupling electrophile. The ortho-iodine on the phenyl ring can undergo Suzuki, Sonogashira, or related coupling reactions after deprotection or after peptide assembly, allowing introduction of boronic acids, alkynes, or other aryl/heteroaryl fragments while maintaining the D-stereocenter. The aromatic substitution pattern can be tuned to modulate hydrophobicity, hydrogen-bonding capacity, and conformational behavior of peptide or peptidomimetic scaffolds. Downstream products include aryl-expanded amino acid derivatives and functionalized peptide intermediates suitable for medicinal chemistry-style optimization and fine chemical synthesis.
3. Chemical Biology Probes
Fmoc-2-Iodo-D-Phenylalanine is suitable for chemical biology applications that require incorporation of a chemically addressable aromatic handle into chiral peptides. The Fmoc-protected amino acid format supports controlled incorporation during peptide synthesis, while the C-I bond provides a platform for subsequent attachment of reporter groups, affinity tags, or modified aromatic motifs through coupling-based conjugation. The D-configuration can be leveraged in probe design to probe stereochemical recognition in binding assays and to generate protease-resistant peptide analogs for mechanistic studies. The iodinated residue enables downstream generation of probe-bearing peptides and derivatized intermediates for analytical research and biomolecular interaction studies.
4. Peptidomimetics And SAR Studies
Fmoc-2-Iodo-D-Phenylalanine is applied in peptidomimetic construction and structure-activity relationship studies where aromatic substitution patterns are systematically varied. The chiral D-amino acid scaffold supports stereochemically defined analog series, while the ortho-iodine enables rapid diversification of the phenyl side chain into substituted aryl or heteroaryl groups that can alter binding interactions. The Fmoc protection strategy allows sequential assembly with other protected amino acids, supporting the generation of analogs that differ primarily at the aromatic electronics and steric profile. The resulting iodinated and cross-coupled analogs function as research intermediates for SAR mapping, fragment-like aromatic tuning, and iterative scaffold refinement in applied peptide chemistry.
5. Process Chemistry Intermediate
Fmoc-2-Iodo-D-Phenylalanine is utilized as a chiral amino acid intermediate in process chemistry routes that require a protected, stereodefined building block with a controllable functional handle. The Fmoc group supports standard manufacturing-compatible protection/deprotection logic for peptide-grade intermediates, while the aryl iodide provides a downstream transformation point for converting the aromatic ring into substituted derivatives without altering the chiral center. The presence of a single, well-defined electrophilic site can simplify route planning for producing iodinated intermediates and subsequent cross-coupling products at scale. The compound can therefore serve as a practical feedstock for specialty chemical production and fine chemical synthesis programs targeting aryl-functionalized amino acid derivatives and peptide building blocks.
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