Boc-2-Iodo-D-Phenylalanine is a Boc-protected, non-natural amino acid derivative featuring a D-phenylalanine backbone bearing an iodine substituent at the 2-position of the side chain aromatic ring. The molecule contains a tert-butoxycarbonyl (Boc) protecting group on the amino functionality and retains a carboxylic acid group, while the aryl iodide provides a halogenated handle that can participate in chemoselective transformations under appropriate conditions. In synthetic chemistry and amino acid derivative workflows, this protected analogue is used as a precursor for preparing substituted phenylalanine-containing peptides or for building aryl-iodide-bearing conjugates used in chemical biology, structure-activity studies, and analytical method development.
CAT No: CP15005
Boc-2-Iodo-D-Phenylalanine is a D-configured phenylalanine derivative bearing a Boc-protected alpha-amino group and a side-chain 2-iodo substituent on the aromatic ring, making it a halogenated, stereodefined amino acid building block. This structure is commonly leveraged in peptide and peptidomimetic synthesis where an aryl iodide provides a convenient handle for downstream functionalization, including cross-coupling strategies, while the Boc protection supports standard amino acid intermediate workflows.
1. Peptide Building Block Use
Boc-2-Iodo-D-Phenylalanine is employed by custom peptide synthesis groups to introduce a halogenated, stereodefined D-phenylalanine residue into peptide sequences. The Boc-protected amino functionality supports conventional protected-amino-acid assembly workflows, enabling incorporation of an aryl iodide-bearing phenylalanine unit that can be retained for later diversification or used as part of a defined analog panel. Researchers developing D-amino-acid-containing peptides for structure-activity relationship studies and proteolysis-resistant analog libraries often select this reagent because the iodinated aromatic side chain provides a synthetically useful differentiation point without altering the backbone stereochemical identity.
2. Cross-Coupling Diversification
Boc-2-Iodo-D-Phenylalanine is widely used in medicinal chemistry and peptidomimetic development as an intermediate that carries an aryl iodide for subsequent C-C bond-forming chemistry. After the amino acid has been incorporated into a peptide fragment or left as a protected intermediate, the iodinated aromatic handle enables diversification via palladium-catalyzed coupling approaches to access substituted phenyl analogs with controlled substitution patterns. This workflow is particularly attractive for teams building structure-defined libraries, where the ability to vary aryl substitution after the stereodefined amino acid step helps streamline analog synthesis and supports systematic SAR campaigns.
3. Pharmaceutical Intermediate Development
Boc-2-Iodo-D-Phenylalanine serves as a specialty pharmaceutical intermediate for preparing iodinated D-phenylalanine derivatives used in downstream synthesis of constrained analogs, linker-bearing fragments, and aryl-substituted peptide building blocks. Process and development chemists value the combination of Boc protection and the aryl iodide functionality because it supports a modular route: the protected amino acid can be carried through intermediate stages while preserving a reactive aryl handle for later conversion to the desired substitution pattern. This makes the reagent a practical choice when a defined D-amino-acid stereocenter must be maintained while enabling late-stage aromatic functionalization in complex intermediate sequences.
4. Analytical Reference Material Support
Boc-2-Iodo-D-Phenylalanine is also used in analytical method development and reference preparation for characterization of iodinated D-phenylalanine-containing intermediates and peptide fragments. Laboratories performing LC-MS or related workflows often rely on structurally defined standards to confirm identity and monitor conversion in synthesis steps involving iodinated aromatic building blocks. The presence of the Boc-protected amino group and the specific 2-iodo substitution pattern provides an unambiguous mass and fragmentation signature that can help validate the presence of the intended stereodefined, halogenated amino acid unit during method optimization and batch qualification experiments.
1. Emu oil in combination with other active ingredients for treating skin imperfections
2. TMEM16F and dynamins control expansive plasma membrane reservoirs
3. Implications of ligand-receptor binding kinetics on GLP-1R signalling
4. An Open-label, Single-center, Safety and Efficacy Study of Eyelash Polygrowth Factor Serum
If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at . We will endeavor to provide highly satisfying products and services.
Creative Peptides is a trusted CDMO partner specializing in high-quality peptide synthesis, conjugation, and manufacturing under strict cGMP compliance. With advanced technology platforms and a team of experienced scientists, we deliver tailored peptide solutions to support drug discovery, clinical development, and cosmetic innovation worldwide.
From custom peptide synthesis to complex peptide-drug conjugates, we provide flexible, end-to-end services designed to accelerate timelines and ensure regulatory excellence. Our commitment to quality, reliability, and innovation has made us a preferred partner across the pharmaceutical, biotechnology, and personal care industries.
Read More