Boc-2-Bromo-D-Phenylalanine is a protected, non-natural amino acid derivative bearing a benzyl side chain substituted with a bromine at the 2-position relative to the alpha carbon, and it is classified as a D-configured phenylalanine analogue. The molecule contains a Boc-protected amino group and a free carboxyl group, with the bromo substituent providing a chemically reactive halogen handle for further functionalization while the stereocenter at the alpha carbon reflects the D configuration indicated in the name. In peptide and amino acid chemistry, this protected bromo-phenylalanine derivative is used as a building block for incorporating the halogenated residue into peptide frameworks and for preparing labeled or conjugatable phenylalanine analogues through subsequent substitution, coupling, or crosslinking chemistry.
CAT No: CP11005
CAS No:261360-76-3
Synonyms/Alias:261360-76-3;Boc-2-bromo-D-phenylalanine;(R)-3-(2-Bromophenyl)-2-((tert-butoxycarbonyl)amino)propanoicacid;Boc-L-phe(2-Br)-OH;Boc-D-2-Bromophenylalanine;Boc-D-2-Bromophe;N-Boc-2-bromo-D-phenylalanine;Boc-D-phe(2-Br)-OH;(2R)-3-(2-bromophenyl)-2-[(tert-butoxycarbonyl)amino]propanoicacid;(R)-N-Boc-2-Bromophenylalanine;BOC-D-2-BR-PHE-OH;BOC-O-BROMO-D-PHE-OH;BOC-D-2-BROMO-PHE-OH;SCHEMBL3560345;CTK8C5110;MolPort-003-793-944;ZINC2244126;ANW-74146;CB-742;N-BOC-D-2-BROMOPHENYLALANINE;AKOS015836526;AB08560;AM82703;AC-16826;AJ-34428
Boc-2-Bromo-D-Phenylalanine is a protected D-phenylalanine building block bearing a Boc-protected amino group and a reactive 2-bromo substituent on the alpha carbon. This stereochemically defined, halogenated amino acid derivative is commonly used in peptide chemistry and medicinal chemistry workflows where controlled installation of a functionalized residue or downstream derivatization from the bromo handle is required. The combination of a stable peptide-compatible protecting group and a site-specific electrophile makes it a practical intermediate for assembling modified peptides and generating structurally defined amino acid derivatives.
1. Modified Peptide Synthesis
Boc-2-Bromo-D-Phenylalanine is used by peptide synthesis groups to introduce a D-configured, alpha-bromo phenylalanine residue into custom peptide sequences, enabling access to peptides with chemically addressable handles at a defined position. Solid-phase or solution-phase peptide assembly teams select this building block when they need a protected amino acid that can be incorporated as a residue while retaining the 2-bromo functionality for subsequent transformations or for generating analog libraries. The Boc protection supports routine coupling workflows, while the stereodefined alpha-bromo substitution provides a direct route to downstream functionalization strategies on the assembled peptide scaffold.
2. Medicinal Chemistry Intermediates
Boc-2-Bromo-D-Phenylalanine is frequently employed in medicinal chemistry and peptidomimetic development as a chiral, electrophile-bearing amino acid intermediate. Process and discovery chemistry teams use the bromo handle to access substituted phenylalanine derivatives and to build structure-activity relationship (SAR) series where alpha-functionalization is a key design element. The Boc-protected amine allows chemists to carry the amino acid through multi-step synthesis while controlling the timing of amine deprotection and further derivatization, supporting the preparation of well-defined analogs for lead optimization.
3. Late-Stage Functionalization Routes
Boc-2-Bromo-D-Phenylalanine supports late-stage derivatization workflows in which a pre-installed electrophilic center is leveraged to introduce new substituents after key assembly steps. Chemical biology and materials-oriented synthesis teams use this reagent when they want to generate site-specific variants from a common protected precursor, using the 2-bromo group as a functional handle for subsequent conversion to alternative side-chain or backbone-modified motifs. The D-configuration and Boc protection help maintain structural fidelity from the intermediate stage through to the final functionalized product, which is particularly valuable when building stereochemically constrained libraries.
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