Cbz-2-Bromo-L-Phenylalanine is a Cbz-protected, halogenated amino acid derivative bearing a benzyl carbamate (Cbz) on the amino group, a carboxylic acid functionality, and a 2-bromo substituent on the alpha carbon with an L-phenylalanine-derived phenyl side chain. The molecule contains both the protected amine and free carboxyl group required for peptide coupling chemistry, while the bromine substituent provides a chemically distinct handle that can participate in further derivatization or stability-relevant studies without altering the core aromatic side-chain character. In synthesis, it is used as a stepwise peptide-building block or intermediate for incorporating an alpha-brominated phenylalanine motif into protected peptide fragments, enabling access to labeled or reactive analogues for structure-activity studies and chemical biology workflows.
CAT No: CP11008
Cbz-2-Bromo-L-Phenylalanine is a chiral, N-Cbz (benzyloxycarbonyl) protected L-phenylalanine derivative bearing a stereogenic center at the α-carbon and a reactive bromine substituent at the 2-position relative to the carboxylate-bearing backbone. The molecule contains a benzyl carbamate on the amino group, a carboxylic acid functionality (or acid-equivalent form depending on handling), and an aryl side chain that supports hydrophobic and π-interaction patterns in peptide and peptidomimetic contexts. The Cbz group provides stable protection during peptide coupling and can be removed under hydrogenolysis-compatible conditions, while the α-bromide functionality can participate in substitution chemistry to enable downstream functionalization. As a chiral amino acid intermediate, the compound is suited to controlled derivatization of the backbone while preserving stereochemical integrity for synthetic organic chemistry and peptide construction workflows.
1. Peptide Synthesis
Cbz-2-Bromo-L-Phenylalanine supports peptide building block preparation where the N-Cbz carbamate protects the amino group during activation of the carboxyl functionality for amide bond formation. The α-bromo substituent can be retained for later backbone modification or converted into alternative side-chain/alpha-functional motifs after incorporation into short peptides or peptide fragments. The combination of a protected amine and a chiral α-center enables stereochemically defined coupling strategies that are compatible with standard protected amino acid chemistry. Resulting peptide analogs can serve as intermediates for further functional group transformations that probe backbone reactivity and structural effects in amino acid and peptide science.
2. Side-Chain Functionalization
Cbz-2-Bromo-L-Phenylalanine functions as an α-brominated amino acid intermediate for nucleophilic substitution and related functional group interconversions that install new substituents at the 2-position. The presence of the Cbz-protected nitrogen helps suppress undesired side reactions during substitution, while the bromide can be leveraged to introduce heteroatom-containing groups, leaving groups, or handles for subsequent coupling chemistry. The phenylalanine side chain preserves aromatic character, supporting downstream design of constrained or electronically tuned amino acid derivatives. The resulting functionalized products can be used to generate stereodefined analog libraries for chemical biology, peptidomimetic construction, and synthetic methodology development.
3. Chiral Building Block Development
Cbz-2-Bromo-L-Phenylalanine is suitable for chiral synthesis routes that require a defined L-configuration at the α-carbon while introducing a reactive electrophilic site for later elaboration. The Cbz carbamate provides a removable protecting group that tolerates many common transformations, allowing the bromide-bearing backbone to be carried through multistep sequences as a controlled stereochemical scaffold. The bromine substituent enables access to chiral derivatives through substitution, elimination/functionalization sequences, or conversion into alternative electrophiles, supporting the preparation of enantiomerically consistent intermediates. Downstream chiral products can serve as building blocks for peptide analogs, stereodefined ligands, and research-grade amino acid derivatives used in structure-focused synthetic design.
4. Chemical Biology Probes
Cbz-2-Bromo-L-Phenylalanine can be applied in chemical biology research where backbone-functionalized amino acid residues are incorporated into peptides to create electrophilic or derivatizable sites for subsequent labeling or capture chemistry. The protected carbamate helps maintain compatibility with peptide assembly conditions, while the α-bromide provides a handle that can be converted into reactive motifs for studying biomolecular interactions or mapping binding environments. The aromatic phenyl side chain supports hydrophobic and π-directed recognition patterns that often influence peptide-protein or peptide-receptor association. Generated labeled or reactive peptide fragments can be used as biochemical research intermediates for developing probes that interrogate molecular recognition and reactivity in controlled experimental settings.
5. Pharmaceutical Intermediate Preparation
Cbz-2-Bromo-L-Phenylalanine serves as a process-relevant intermediate in fine chemical synthesis for producing protected amino acid derivatives used in medicinal chemistry and peptidomimetic programs. The N-Cbz protection strategy supports manufacturing-friendly handling during carboxyl activation and subsequent coupling steps, while the stereodefined α-bromide enables conversion into alternative functional groups that can be required in downstream drug-like scaffolds. The phenylalanine aryl side chain provides a common motif for SAR-focused analog generation, and the electrophilic backbone position can be used to diversify chemical space without losing stereochemical control. Downstream products derived from this intermediate can be routed into peptide-like inhibitors, backbone-modified analogs, or other chiral intermediates used in applied synthetic development.
6. Analytical Research Standards
Cbz-2-Bromo-L-Phenylalanine can be used in analytical research as a structurally defined reference material for monitoring amino acid derivative stability, protecting-group behavior, and backbone functional group transformations. The combination of a Cbz-protected amine and an α-bromide enables characteristic chromatographic and spectroscopic signatures that can support method development for protected amino acids, peptide coupling intermediates, and derivatization products. The defined L-stereochemistry aids in distinguishing stereoisomeric or partially transformed species during synthetic process evaluation. Analytical standards derived from this scaffold can support quality control of peptide building block preparation, intermediate characterization, and verification of backbone modification pathways in research and industrial chemical manufacturing contexts.
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