Boc-D-Bpa-OH is a protected amino acid derivative featuring a D-configured β-(benzyl)phenylalanine (Bpa) side chain, where the amino functionality is protected as a Boc (tert-butoxycarbonyl) carbamate and the molecule also bears a free carboxylic acid group. The benzyl-substituted aromatic side chain provides a hydrophobic, π-rich functionality that can be used as a structural element in peptide frameworks, while the Boc group controls chemoselectivity by masking the amino group during stepwise coupling chemistry. In peptide synthesis and related chemical biology workflows, Boc-D-Bpa-OH functions as a protected building block for incorporating the Bpa residue into peptides or peptide intermediates for structure-activity studies, labeling strategies, or preparation of more complex amino acid derivatives.
CAT No: CP25192
CAS No:117666-94-1
Synonyms/Alias:117666-94-1;Boc-D-Bpa-OH;Boc-4-benzoyl-D-phenylalanine;(R)-3-(4-Benzoylphenyl)-2-((tert-butoxycarbonyl)amino)propanoicacid;Boc-D-4-Benzoylphenylalanine;Boc-D-4-Benzoylalanine;AmbotzBAA1347;SCHEMBL12984836;09776_FLUKA;CTK8C5198;MolPort-003-795-017;ZINC2560865;ANW-74585;AKOS015836424;CB-1273;RTR-003107;AJ-40667;AK-43456;SC-21309;KB-251120;TL8000489;ST24035430;K-1215;(2R)-3-(4-benzoylphenyl)-2-[(tert-butoxycarbonyl)amino]propanoicacid;(R)-2-[(tert-Butoxycarbonyl)amino]-3-(4-benzoylphenyl)propanoicacid
Chemical Name:N-alpha-t-Butyloxycarbonyl-4-benzoyl-D-phenylalanine
Boc-D-Bpa-OH is a Boc-protected D-amino acid featuring an aromatic side chain designed for chemical biology workflows, with the stereochemistry fixed at the D-configuration. The Boc group provides a protected amino functionality for controlled incorporation into peptide sequences, while the side-chain architecture supports use as a photoactive amino acid building block in peptide and protein labeling strategies.
1. Photoaffinity Peptide Labeling
Boc-D-Bpa-OH is used as a photoaffinity amino acid building block for preparing peptides that can form covalent contacts with nearby biomolecular targets upon light activation. Researchers in chemical biology and proteomics workflows incorporate this D-amino acid into peptide probes to enable target proximity mapping, helping distinguish direct binding interfaces from non-specific associations. The Boc protection supports reliable peptide assembly into defined sequences used in pull-down or downstream analytical characterization.
2. Site-Specific Protein Probing
Boc-D-Bpa-OH supports site-specific interrogation of protein interaction surfaces by enabling the construction of peptides or peptide segments containing a single, defined photoactive residue. In protein interaction mapping and structural studies, developers use these photo-crosslinking peptides to capture transient or weak interactions under controlled conditions, then analyze crosslinked products by gel-based or mass spectrometry workflows. The D-configuration and protected amino functionality help maintain sequence fidelity during synthesis, which is critical for interpreting crosslinking patterns.
3. Peptide Library Synthesis
Boc-D-Bpa-OH is frequently selected for peptide library construction where photo-crosslinking capability is desired alongside systematic variation of surrounding residues. Peptide chemists use this Boc-protected building block to generate focused libraries for screening interaction motifs, optimizing labeling efficiency, or comparing crosslinking behavior across sequence contexts. By providing a protected amino acid suitable for stepwise peptide assembly, it integrates into established peptide synthesis pipelines used to generate multiple probe candidates for chemical biology experiments.
4. Chemical Biology Tool Development
Boc-D-Bpa-OH is applied in the development of specialized chemical biology tools that require a photoactivatable amino acid handle embedded within a peptide framework. Probe developers incorporate this residue into affinity or recognition peptides to create reagents for mapping binding neighborhoods, validating interaction models, and generating structurally informative crosslinked adducts for subsequent characterization. The protected amino functionality and stereochemical control make it practical for producing reproducible probe batches used in iterative tool refinement.
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