Boc-L-Bpa-OH is a protected, amino acid derivative featuring an L-configured backbone bearing a benzyl-protected side chain that corresponds to the Bpa (benzoyl-phenylalanine) class of photo-crosslinking amino acids. The molecule contains an N-terminal Boc (tert-butoxycarbonyl) protecting group and a free carboxylic acid, while the side chain incorporates a benzophenone functionality that can participate in photochemical crosslinking under appropriate irradiation conditions. Boc-L-Bpa-OH is used as a precursor for incorporating the Bpa residue into peptides during stepwise or solid-phase peptide synthesis, enabling structure-interaction studies and chemical biology workflows that require a photo-reactive handle within a defined peptide context.
CAT No: CP25132
CAS No:104504-43-0
Synonyms/Alias:104504-43-0;Boc-Bpa-OH;Boc-4-benzoyl-L-phenylalanine;(S)-3-(4-Benzoylphenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid;(2S)-3-(4-benzoylphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic Acid;Boc-p-Bz-Phe-OH;(2S)-3-(4-benzoylphenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid;MFCD00151886;Boc-Phe(4-Bzo)-OH;Boc-p-benzoylphenylalanine;SCHEMBL5065660;DTXSID90426770;HIQJNYPOWPXYIC-KRWDZBQOSA-N;L-Phenylalanine, 4-benzoyl-N-[(1,1-dimethylethoxy)carbonyl]-;AKOS015836543;AKOS015912005;CS-W013890;Boc-Bpa-OH, >=96.0% (HPLC);PS-12873;A50147;4-benzoyl-N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine;4-Benzoyl-N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine;;N-alpha-t-Butyloxycarbonyl-4-benZoyl-L-phenylalanine (Boc-L-Bpa-OH);
Chemical Name:N-alpha-t-Butyloxycarbonyl-4-benzoyl-L-phenylalanine
Boc-L-Bpa-OH is a Boc-protected L-amino acid derivative built on the benzylated phenylalanine-like side chain of Bpa (benzoyl-phenylalanine), providing a protected amino group for peptide assembly and a benzophenone-type photo-crosslinking functionality on the aromatic side chain. This reagent is widely used to introduce a photoactivatable crosslinking site into peptides and protein constructs, enabling covalent capture of transient or weak biomolecular interactions upon light activation. The Boc protection supports standard protected amino acid handling during peptide synthesis workflows and downstream purification of the modified sequences.
1. Photoaffinity Peptide Probes
Boc-L-Bpa-OH is used to incorporate a photo-crosslinkable amino acid residue into peptides for interaction mapping and target engagement studies. Researchers in chemical biology and protein chemistry rely on its Boc-protected amino functionality to assemble modified peptide sequences, while the benzophenone-type side-chain enables covalent linkage to nearby binding partners after photoactivation. This approach is commonly applied to identify or validate contact regions in ligand-protein, peptide-receptor, or protein-protein recognition systems, where conventional noncovalent assays may fail to stabilize transient complexes.
2. Protein Interaction Mapping
Boc-L-Bpa-OH supports site-specific photo-crosslinking experiments in protein engineering workflows that require covalent trapping of interaction interfaces. In practice, it is incorporated into peptides used as probes, or into protein fragments and engineered constructs where researchers need a defined crosslinking handle at a chosen position. The reagent's protected backbone functionality streamlines its use in peptide segment preparation, and the photoactivatable aromatic crosslinker provides a robust strategy for capturing proximal residues during binding events, followed by analysis of crosslinked species using SDS-PAGE, immunoblotting, or mass spectrometry.
3. Structural Proteomics Workflows
Boc-L-Bpa-OH is frequently selected for spatial and interface-focused proteomics workflows that aim to characterize interaction networks and proximity relationships in complex mixtures. Scientists use Bpa-containing peptides or Bpa-modified protein fragments as photo-crosslinking reagents to generate covalent adducts that better withstand washing and separation steps than noncovalent complexes. The Boc-protected amino acid form is particularly practical for preparing defined Bpa-bearing reagents in controlled stoichiometries, enabling downstream identification of crosslinked partners and mapping of contact sites through LC-MS/MS-based analysis.
4. Peptide Library Crosslinking
Boc-L-Bpa-OH is applied in peptide library development where photo-crosslinking is used as an orthogonal readout for binding and specificity screening. Peptide chemists incorporate this residue into positional or sequence-varied libraries to compare interaction patterns across related motifs, using light-triggered covalent capture to enrich for true binding events. The protected amino acid format supports consistent incorporation during parallel peptide synthesis, and the photoactivatable crosslinking side chain provides a direct linkage between binding occurrence and recoverable crosslinked products for subsequent analytical characterization.
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