Boc-D-Bip-OH is a protected amino acid derivative featuring a Boc (tert-butoxycarbonyl) carbamate protecting group on the amino functionality and a biphenyl (Bip) side chain that renders the molecule predominantly hydrophobic and aromatic. The structure contains both an N-protected amino group and a free carboxylic acid (-CO2H), with the "D" designation indicating the stereochemical form of the chiral amino acid center as specified by the product name. Boc-D-Bip-OH is used as a building block in stepwise peptide synthesis and related coupling strategies where temporary protection of the amine and controlled chemoselectivity are required for assembling amino acid sequences or for preparing further biphenyl-substituted peptide and conjugate analogues.
CAT No: CP25287
CAS No:128779-47-5
Synonyms/Alias:128779-47-5;BOC-D-4,4'-BIPHENYLALANINE;Boc-3-(4-Biphenylyl)-D-alanine;Boc-D-4,4-Biphenylalanine;(R)-3-([1,1'-BIPHENYL]-4-YL)-2-((TERT-BUTOXYCARBONYL)AMINO)PROPANOIC ACID;BOC-D-4-PHENYLPHENYLALANINE;BOC-4-BIPHENYL-D-ALA;(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(4-phenylphenyl)propanoic acid;[1,1'-Biphenyl]-4-propanoic acid, alpha-[[(1,1-dimethylethoxy)carbonyl]amino]-, (alphaR)-;BOC-D-BPH-OH;(2R)-3-([1,1'-Biphenyl]-4-yl)-2-[(tert-butoxycarbonyl)amino]propanoic acid;(2R)-3-{[1,1'-BIPHENYL]-4-YL}-2-[(TERT-BUTOXYCARBONYL)AMINO]PROPANOIC ACID;MFCD00191185;SCHEMBL1326276;DTXSID20427078;NBVVKAUSAGHTSU-QGZVFWFLSA-N;BCP14591;N-Boc-3-(4-biphenylyl)-D-alanine;(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-(4-phenylphenyl)propanoic acid;AKOS016842314;AC-9870;CS-W023100;DS-1074;EN300-3404696;(R)-3-biphenyl-4-yl-2-t-butoxycarbonylamino-propionic acid;(R)-3-([1,1'-BIPHENYL]-4-YL)-2-(BOC-AMINO)PROPANOIC ACID;(R)-3-(BIPHENYL-4-YL)-2-(TERT-BUTOXYCARBONYLAMINO)PROPANOIC ACID;(2R)-3-(BIPHENYL-4-YL)-2-[(TERT-BUTOXYCARBONYL)AMINO]PROPANOIC ACID;(2R)-3-{[1,1'-biphenyl]-4-yl}-2-{[(tert-butoxy)carbonyl]amino}propanoic acid;(R)-3-([1,1'-BIPHENYL]-4-YL)-2-((TERT-BUTOXYCARBONYL)AMINO)PROPANOICACID;(aR)-a-[[(1,1-Dimethylethoxy)carbonyl]amino]-[1,1'-biphenyl]-4-propanoic Acid; (R)-a-[[(1,1-Dimethylethoxy)carbonyl]amino]-[1,1'-biphenyl]-4-propanoic Acid; (R)-3-(Biphenyl-4-yl)-2-[(tert-butoxycarbonyl)amino]propionic Acid;852-973-3;
Chemical Name:(R)-N-alpha-t-Butyloxycarbonyl-biphenylalanine
Boc-D-Bip-OH is a protected D-amino acid building block bearing a Boc-protected amino group and a biphenyl-type side chain (Bip) that provides pronounced hydrophobic and conformationally rigid character. As a Boc-protected amino acid, it is commonly selected for controlled incorporation of a D-configured residue into peptide segments during protected-amino-acid synthesis workflows. Its protected form supports downstream coupling strategies used in custom peptide manufacturing and medicinal chemistry programs where stereochemical control and side-chain hydrophobicity are important.
1. D-Peptide Segment Building
Boc-D-Bip-OH is used as a stereodefined residue for assembling peptide segments that require a D-configuration at a specific position. Peptide chemists and custom peptide synthesis providers rely on Boc-protected amino acids to build well-defined sequences with controlled side-chain hydrophobicity, where the biphenyl-type Bip side chain helps tune local packing, aromatic content, and overall physicochemical character. This makes the reagent a practical choice for preparing D-containing peptides, peptidomimetic scaffolds, and structure-activity relationship (SAR) libraries in medicinal chemistry.
2. Hydrophobic Side-Chain Tuning
Boc-D-Bip-OH supports the rational design of peptide-like molecules where introducing a bulky, aromatic, hydrophobic side chain is used to modulate solubility, aggregation propensity, and conformational preferences. Research groups developing protease-resistant or metabolically durable peptidomimetic analogs often incorporate D-amino acid residues alongside aromatic side chains to shape the microenvironment around binding motifs and to refine structure-property relationships. In this workflow, the protected Boc amino functionality enables consistent peptide assembly while the Bip side chain provides the key chemical handle for hydrophobic tuning.
3. Medicinal Chemistry Intermediate Supply
Boc-D-Bip-OH is also used as a pharmaceutical intermediate building block in medicinal chemistry and specialty chemical manufacturing, where protected amino acid derivatives are required for downstream derivatization into larger targets. Process development teams and synthetic chemistry groups incorporate this type of Boc-protected, stereodefined amino acid into advanced intermediates for analog generation, enabling efficient route planning for final coupling steps and late-stage functionalization. The combination of D stereochemistry and a biphenyl-type side chain makes it particularly relevant when aromatic, hydrophobic character must be built into the target framework early in the synthesis sequence.
4. Stereocontrolled Library Synthesis
Boc-D-Bip-OH is frequently selected for generating stereochemically defined peptide or peptidomimetic libraries, where comparing sequences that differ by a single residue is used to map structure-activity relationships. In screening-focused chemistry workflows, the reagent's D-configuration and protected amino group help ensure that each library member contains the intended stereochemical arrangement and side-chain identity, improving interpretability of SAR outcomes. Custom synthesis groups use this protected amino acid to standardize segment preparation while varying neighboring residues, enabling systematic evaluation of how aromatic hydrophobic substitution influences overall molecular behavior.
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