Cbz-2-Fluoro-D-Phenylalanine is a protected, non-natural amino acid derivative featuring a phenylalanine backbone bearing a fluorine substituent at the 2-position of the side chain and a D stereochemical configuration as indicated by the name. The molecule contains an N-terminal benzyloxycarbonyl (Cbz) protecting group on the amino functionality and a free carboxylic acid, while the fluorinated side chain introduces a distinct electronegative substituent that can modulate steric and electronic properties during peptide coupling. In peptide chemistry and chemical biology research, this protected fluoro-substituted amino acid is used as a building block for incorporating fluorinated residues into peptides and for structure-activity or labeling studies where a defined C-F functional handle and controlled protection of the amine are required.
CAT No: CP14409
Cbz-2-Fluoro-D-Phenylalanine is a D-configured, fluorinated phenylalanine derivative bearing a benzyloxycarbonyl (Cbz) protecting group on the amino functionality and a 2-fluoro substituent at the alpha position. The molecule combines a chiral amino acid backbone with an aryl side chain, while the C-F bond at C2 introduces distinct electronic effects and stereochemical constraints that can influence peptide coupling behavior and downstream transformations. The protected amine and the fluorinated stereocenter make it suitable for controlled deprotection and for incorporation into peptide-like frameworks where fluorine serves as a physicochemical probe or metabolic-stability handle. The presence of the Cbz carbamate also supports standard orthogonal protection strategies during protected amino acid synthesis and iterative peptide construction.
1. Peptide Synthesis
Cbz-2-Fluoro-D-Phenylalanine is applied in peptide building workflows where a protected amino acid with a defined stereocenter is required for stepwise coupling. The Cbz-protected amine and the amino acid backbone enable amide bond formation under peptide synthesis conditions, while the 2-fluoro substituent can be retained to introduce fluorinated analogs into peptide sequences. D-configuration supports stereochemically defined incorporation for generating D-amino acid containing peptides and peptidomimetics with controlled backbone chirality. Downstream, deprotection of the Cbz group allows sequential assembly or conversion into further functionalized derivatives for structure-activity relationship studies.
2. Peptidomimetics And SAR
Cbz-2-Fluoro-D-Phenylalanine is used in peptidomimetic design and SAR-oriented chemical biology programs that require fluorinated amino acid analogs. The 2-fluoro group provides a compact substituent that can modulate polarity, hydrogen-bonding patterns, and conformational preferences when embedded into peptide scaffolds. The phenyl side chain supports aromatic interactions, and the D-stereochemistry enables systematic exploration of stereochemical effects on molecular recognition. The Cbz-protected amine supports consistent handling as a chiral intermediate for generating libraries of fluorinated peptide analogs and for preparing reference compounds used in SAR comparisons.
3. Chemical Biology Labeling
Cbz-2-Fluoro-D-Phenylalanine serves as a fluorine-containing amino acid precursor for chemical biology workflows that rely on spectroscopic or mechanistic labeling. The C-F bond can be leveraged for 19F NMR tracking and for monitoring incorporation or transformations in fluorinated biomolecule analogs, while the aromatic side chain can participate in binding-site interactions. The Cbz carbamate allows controlled deprotection to expose the amine for conjugation steps or for generating fluorinated residues in peptide-based probes. The resulting fluorinated derivatives can be employed as analytical and mechanistic tools for studying amino acid incorporation, peptide stability, and structure-dependent reactivity in biochemical research settings.
4. Protected Amino Acid Chemistry
Cbz-2-Fluoro-D-Phenylalanine is suitable for protected amino acid intermediate preparation where orthogonal protection and stereochemical fidelity are central. The Cbz group functions as a removable N-protection handle, supporting sequential protection/deprotection logic during synthesis of fluorinated amino acid derivatives and peptide building blocks. The alpha-fluorinated stereocenter can participate in downstream derivatization strategies, including transformations that preserve chirality while altering functional group environments around the backbone. The compound's defined configuration and protected functionality make it a practical chiral starting material for manufacturing-grade fine chemical synthesis of fluorinated amino acid intermediates.
5. Process Chemistry Intermediate
Cbz-2-Fluoro-D-Phenylalanine is used as a chiral fluorinated intermediate in process chemistry routes targeting fluorinated amino acid derivatives for research and industrial manufacturing. The combination of a stable Cbz-protected carbamate and a fluorinated alpha position supports controlled handling through protection-compatible steps, enabling scalable synthesis of peptide-coupling-ready building blocks. The D-configuration reduces stereochemical ambiguity in downstream coupling and minimizes the need for extensive stereochemical correction during intermediate preparation. The resulting material can be integrated into industrial fine chemical production of fluorinated peptide analogs, peptidomimetics, and other amino acid-derived specialty compounds.
1. Implications of ligand-receptor binding kinetics on GLP-1R signalling
4. TMEM16F and dynamins control expansive plasma membrane reservoirs
5. Adipose tissue is a key organ for the beneficial effects of GLP-2 metabolic function
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