Fmoc-2-Bromo-L-Phenylalanine is an Fmoc-protected amino acid derivative featuring the L-phenylalanine backbone with a bromine substituent at the 2-position relative to the amino acid carbon framework, placing it in the class of halogenated, nonstandard amino acid building blocks for peptide chemistry. The molecule contains an Fmoc carbamate protecting group on the amino functionality and a free carboxylic acid group, while the side chain retains a benzyl phenyl ring and the 2-bromo substitution introduces a reactive halogen handle for chemical diversification and structure-activity studies. In synthetic workflows, it is employed as a protected amino acid precursor for stepwise peptide assembly and as a substrate for preparing halogen-functionalized peptide analogues and related labeled or conjugatable derivatives.
CAT No: CP11006
Fmoc-2-Bromo-L-Phenylalanine is an Fmoc-protected L-phenylalanine derivative bearing a stereogenic, side-chain-substituted bromine at the alpha position (2-bromo) relative to the carboxylate-bearing carbon framework. The molecule contains an Fmoc carbamate on the amino group, a free carboxyl functionality or carboxyl derivative depending on handling, and a benzylic aromatic ring that supports hydrophobic and π-interaction features in peptide contexts. The C-Br bond at the 2-position provides a reactive handle for nucleophilic substitution, metal-catalyzed cross-coupling, and derivatization into alternative side-chain or backbone functionalities while retaining the chiral L-configuration. The combination of a protected amine and a halogenated chiral center makes the compound a chiral amino acid intermediate suitable for peptide coupling chemistry and downstream synthetic modification.
1. Peptide Synthesis
Fmoc-2-Bromo-L-Phenylalanine supports solid-phase peptide synthesis workflows where an Fmoc-protected amino acid building block is required for controlled N-deprotection and subsequent coupling. The Fmoc carbamate enables standard base-mediated removal to generate a reactive amine for peptide bond formation, while the L-stereocenter and the aromatic side chain preserve defined backbone stereochemistry and side-chain recognition elements. The 2-bromo functionality can be retained through peptide assembly or selectively transformed after incorporation to generate backbone-modified analogs, enabling peptide coupling chemistry followed by post-assembly functionalization. The resulting halogenated peptide scaffolds can be used to probe stereochemical effects and reactivity patterns in peptide science and chemical biology research.
2. Peptidomimetic Construction
Fmoc-2-Bromo-L-Phenylalanine serves as a chiral precursor for peptidomimetic and backbone-modified scaffold construction where the alpha-brominated stereocenter provides a handle for converting a peptide-like framework into alternative functional motifs. The Fmoc-protected amine allows incorporation into peptide sequences or peptide analogs, while the bromine at the 2-position can be converted into nucleophile-derived substituents, enabling access to substituted amino acid analogs that mimic or reshape hydrogen-bonding and steric profiles. The phenyl side chain contributes aromatic surface area for molecular recognition, supporting structure-activity relationship studies that compare halogenated versus substituted variants. Downstream derivatization from the bromo intermediate can feed fragment elaboration and synthetic library generation for peptidomimetic design.
3. Side-Chain Functionalization
Fmoc-2-Bromo-L-Phenylalanine enables side-chain and backbone functionalization strategies driven by the reactivity of the C-Br bond under substitution and cross-coupling conditions. The compound's protected amino group (Fmoc) helps isolate the reactive halogen during synthetic sequences that require temporary amine masking, allowing selective transformations on the halogenated chiral center before or after deprotection. The presence of a chiral L-configuration supports stereochemical retention or controlled stereochemical outcomes depending on the transformation pathway, which is relevant for generating stereodefined amino acid derivatives. The resulting functionalized amino acid intermediates can be used to build non-natural amino acid derivatives for medicinal chemistry research and applied synthetic organic chemistry.
4. Chemical Biology Probes
Fmoc-2-Bromo-L-Phenylalanine can be applied in chemical biology research to create reactive peptide or protein labeling probes that incorporate a defined stereocenter and a tunable electrophilic handle. The Fmoc group supports incorporation into peptide sequences, while the alpha-bromine can be leveraged to introduce functional groups that participate in selective conjugation chemistry after peptide assembly. The phenylalanine aromatic ring can aid in maintaining binding-relevant hydrophobic interactions during probe design, supporting molecular recognition in target engagement experiments. Downstream conversion of the bromo functionality into conjugation-ready motifs enables generation of labeling reagents, affinity handles, and chemically addressable biomolecule analogs for mechanistic studies.
5. Process Chemistry Intermediate
Fmoc-2-Bromo-L-Phenylalanine functions as a chiral amino acid intermediate for process chemistry and fine chemical synthesis where orthogonal protection of the amine and a defined reactive halogen support modular manufacturing routes. The Fmoc-protected nitrogen allows predictable deprotection and coupling steps in peptide-building operations, while the brominated chiral center provides a branch point for converting to alternative functional group patterns without changing the core L-phenylalanine framework. The compound's structural features can be used to design scalable intermediate sequences that separate amine-handling from halogen-functionalization steps, supporting robust intermediate preparation for downstream specialty chemicals. The resulting derivatives can serve as feedstocks for peptide analog production, chiral building block supply, and industrial synthesis of halogen-to-functional-group transformed amino acid products.
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