Boc-4-Bromo-L-Phenylalanine is a Boc-protected, L-configured amino acid derivative belonging to the phenylalanine family, featuring a benzyl side chain bearing a para-bromo substituent. The molecule contains a free carboxylic acid and an N-terminus protected as a tert-butoxycarbonyl (Boc) carbamate, with the aromatic side chain functionalized for halogen-directed reactivity while maintaining the stereochemical identity indicated by the "L" designation. It is used in peptide synthesis and amino acid building-block workflows where the Boc group supports chemoselective coupling at the amino function, and the aryl bromide provides a handle for downstream derivatization in structure-activity studies or chemical biology conjugation strategies.
Boc-4-Bromo-L-Phenylalanine is an L-phenylalanine derivative bearing a para-bromo substituent on the aromatic ring and an N-Boc protecting group, making it a stable, isolable building block for peptide and peptidomimetic synthesis. The combination of an aniline-free aromatic bromide and a protected amino terminus supports downstream diversification where the aryl bromide serves as a handle for cross-coupling or late-stage functionalization. In research workflows, this compound is commonly selected when an aryl halide must be preserved through peptide assembly and then converted into a tailored substituent for SAR studies or probe development.
1. Peptide Synthesis Building Block
Boc-4-Bromo-L-Phenylalanine is used in custom peptide synthesis workflows where an N-Boc-protected amino acid segment is required while retaining an aryl bromide for subsequent derivatization. Peptide chemists incorporate this residue into protected peptide fragments or final peptide sequences using standard protected-amino-acid coupling strategies, benefiting from the orthogonality of the N-Boc group during assembly and the stability of the bromo substituent under typical peptide coupling and purification conditions. The preserved para-bromophenyl motif enables later conversion to substituted phenyl variants without changing the peptide backbone, supporting structure-activity relationship (SAR) campaigns and analog generation for research peptides.
2. Late-Stage Aryl Functionalization
Boc-4-Bromo-L-Phenylalanine is frequently selected as a precursor for late-stage diversification of peptide scaffolds and peptidomimetic intermediates via aryl bromide chemistry. After peptide assembly, the para-bromo group provides a practical electrophilic site for cross-coupling-based installation of new aromatic substituents, allowing medicinal chemistry teams to rapidly generate analog series while keeping the rest of the molecule intact. This approach is especially useful when the desired substituent pattern is not known at the outset of synthesis, or when iterative library construction is needed for binding studies, chemical biology probes, or receptor/target interaction mapping using structurally related peptide analogs.
3. Medicinal Chemistry SAR Analogues
Boc-4-Bromo-L-Phenylalanine supports medicinal chemistry programs that require defined aromatic substitution patterns on phenylalanine-based motifs. Researchers use this building block to introduce a para-brominated phenylalanine residue into peptide-like candidates and then transform the aryl bromide into functional substituents that tune electronic properties, steric profile, or physicochemical characteristics relevant to SAR. Because the amino group is protected as Boc, the reagent integrates cleanly into protected intermediate synthesis and segment coupling strategies, helping teams maintain consistent stereochemistry at the alpha-carbon while varying the aromatic ring substitution to build focused analog sets.
4. Pharmaceutical Intermediate Diversification
Boc-4-Bromo-L-Phenylalanine is also used as a pharmaceutical intermediate for preparing brominated aromatic amino acid derivatives that serve as inputs to further synthetic elaboration. Process and development chemists value the combination of a protected amino functionality and a reactive aryl bromide, since it allows conversion into a range of substituted phenylalanine derivatives that can feed downstream steps for specialty building blocks, reference materials, or advanced intermediates used in peptide-derived chemistry. This makes the compound a practical choice when preserving a single, well-defined functional handle through early stages of synthesis is advantageous for controlling the order of diversification steps.
1. Immune-awakening Saccharomyces-inspired nanocarrier for oral target delivery to lymph and tumors
2. Adipose tissue is a key organ for the beneficial effects of GLP-2 metabolic function
5. Immune responses to homocitrulline-and citrulline-containing peptides in rheumatoid arthritis
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