Boc-L-Bip-OH contains an L-amino acid framework bearing a biphenyl side chain, classifying it as a protected amino acid derivative with a bulky, hydrophobic aromatic functionality. The molecule features a free carboxylic acid and an amino group masked as a Boc carbamate, which suppresses undesired amine reactivity during coupling and supports chemoselective stepwise peptide assembly. In synthesis and chemical biology workflows, it is used as a protected building block for incorporating a biphenyl-containing residue into peptides or peptide-related intermediates, and as a precursor for further functionalization of the aromatic side chain after deprotection.
CAT No: CP25371
CAS No:147923-08-8
Synonyms/Alias:147923-08-8;Boc-L-4,4'-Biphenylalanine;Boc-4-phenyl-Phe-OH;(S)-3-([1,1'-Biphenyl]-4-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid;Boc-Bip-OH;Boc-Bip(4,4')-OH;BOC-4-BIPHENYL-L-ALA;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(4-phenylphenyl)propanoic acid;N-Boc-4-phenyl-L-phenylalanine;Boc-3-(4-Biphenylyl)-L-alanine;[1,1'-Biphenyl]-4-propanoic acid, alpha-[[(1,1-dimethylethoxy)carbonyl]amino]-, (alphaS)-;(S)-3-(biphenyl-4-yl)-2-(tert-butoxycarbonylamino)propanoic acid;Boc-4-phenyl-L-phenylalanine;Boc-D-Bip-OH;N-alpha-t-Butyloxycarbonyl-L-biphenylalanine (Boc-L-Bip-OH);BOC-P-PHENYL-L-PHENYLALANINE;MFCD00191184;N-(tert-Butoxycarbonyl)-4-phenyl-L-phenylalanine;BOC-L-4,4'-BIPHENYLPHENYLALANINE;(2S)-3-([1,1'-Biphenyl]-4-yl)-2-[(tert-butoxycarbonyl)amino]propanoic acid;(2S)-3-{[1,1'-BIPHENYL]-4-YL}-2-[(TERT-BUTOXYCARBONYL)AMINO]PROPANOIC ACID;BOC-BPH-OH;(2S)-2-{[(Tert-Butoxy)Carbonyl]Amino}-3-(4-Phenylphenyl)Propanoic Acid;Boc-L-4,4-biphenylalanine;SCHEMBL1325182;Boc-4-phenyl-Phe-OH, 97%;DTXSID20375924;NBVVKAUSAGHTSU-KRWDZBQOSA-N;AKOS015912048;AC-9869;FB47980;HY-78843;PS-12517;Boc--(4-biphenylyl)-Ala-OH;Boc-Bip-OH;B4289;CS-0009337;N12087;EN300-3404695;Nalpha-tert-butoxycarbonyl-4-phenyl-phenylalanine;(S)-2-t-Butoxycarbonylamino-3-biphenyl-4-yl-propionic acid;(2S)-3-biphenyl-4-yl-2-tert-butoxycarbonylamino-propionic acid;(S)-2-(t-Butoxycarbonylamino)-3-(biphenyl-4-yl)propionic acid;(S)-2-t-butoxycarbonylamino-3-(biphenyl-4-yl)-propionic acid;(S)-2(-t-butoxycarbonylamino)-3-(biphenyl-4-yl)-propionic acid;(S)-2-(t-butoxycarbonylamino)-3-(biphenyl-4-yl)-propionic acid;979-741-5;Boc-L-Bip(4,4')-OH;Boc-L-Ala(4,4'-biphenyl)-OH;(S)-2-(Boc-amino)-3-(4-biphenylyl)propionic acid;
Chemical Name:N-alpha-t-Butyloxycarbonyl-L-biphenylalanine
Boc-L-Bip-OH is a Boc-protected, L-configured amino acid building block featuring a biphenyl (Bip) side chain, providing a rigid, hydrophobic aromatic motif for medicinal chemistry and peptide-based materials. The N-terminal Boc protection makes it a practical substrate for protected-amino-acid workflows, while the bulky aromatic side chain supports incorporation into peptides and peptide mimetics where hydrophobic packing and conformational bias are desired. As a protected amino acid, it is typically handled as a synthesis intermediate for downstream coupling into larger structures rather than as a free amino acid reagent for biological assays.
1. Peptide Building Block
Boc-L-Bip-OH is used as an aromatic side-chain amino acid building block for custom peptide synthesis where a hydrophobic biphenyl residue is required for structure-property studies. Peptide chemists commonly incorporate this residue into short peptide segments to probe how steric bulk and aromatic surface area influence folding propensity, aggregation behavior, and binding-site microenvironment in receptor/ligand interaction models. Its Boc-protected amino functionality supports routine protected-amino-acid assembly workflows, enabling consistent incorporation of the biphenyl motif into peptide sequences for research-grade peptide libraries and structure-activity relationship (SAR) development.
2. Peptidomimetic And SAR
Boc-L-Bip-OH is frequently selected in medicinal chemistry programs to introduce a biphenyl hydrophobe as part of peptidomimetic scaffolds and constrained analog series. Medicinal and process development teams use this building block to prepare amide-linked intermediates and peptide-like structures that emulate key hydrophobic contacts while maintaining an amino-acid-derived stereochemical handle. The Boc protection supports controlled stepwise synthesis toward larger fragments, which is particularly useful when the biphenyl side chain must be introduced early or preserved through subsequent coupling and functional group manipulation during SAR campaigns.
3. Pharmaceutical Intermediate Development
Boc-L-Bip-OH serves as a protected amino acid intermediate for manufacturing and development of aromatic amide-containing intermediates used in downstream API-adjacent chemical space exploration. Process chemists and synthetic development groups rely on Boc protection to manage chemoselectivity during fragment assembly, especially when preparing coupling-ready intermediates that incorporate the biphenyl motif. The rigid, hydrophobic side chain provided by the biphenyl group is valuable for generating libraries of hydrophobic-rich intermediates used in lead optimization, where aromatic content and steric profile are tuned to support potency and selectivity hypotheses in non-clinical research workflows.
4. Hydrophobic Biomaterials Precursors
Boc-L-Bip-OH is also used to prepare aromatic, hydrophobic monomeric or oligomeric segments for biomaterials research where enhanced hydrophobic interactions and π-π stacking can contribute to material organization. Materials scientists incorporate biphenyl-containing amino acid derivatives into peptide-based polymers or crosslinkable fragments to study how aromatic content affects self-assembly, surface interactions, and network formation in model systems. The Boc-protected amino functionality supports stepwise synthesis of material precursors that can later be coupled or transformed into larger polymer architectures for controlled materials development.
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