Boc-D-homoPhenylalanine is a protected, non-natural amino acid derivative featuring a D-configured amino acid backbone bearing an extended "homo" phenylalanine side chain and a benzyl-like aromatic ring. The molecule contains an N-Boc (tert-butoxycarbonyl) protecting group on the amino functionality and a free carboxylic acid, with the side chain presenting a hydrophobic aromatic group suitable for residue-level structure-property studies in peptide frameworks. In synthesis, the Boc-protected amine supports stepwise coupling strategies for preparing peptides and peptide analogues, while the D stereochemistry and elongated aromatic side chain provide a handle for studying stereochemical effects and side-chain length-dependent conformational or binding behavior in chemical biology and protein engineering workflows.
CAT No: CP17405
CAS No:82732-07-8
Synonyms/Alias:Boc-D-homophenylalanine;82732-07-8;Boc-D-Homophe-OH;BOC-D-HOMO-PHE;(R)-2-((tert-Butoxycarbonyl)amino)-4-phenylbutanoicacid;BOC-D-HOPHE-OH;(2R)-2-[(tert-butoxycarbonyl)amino]-4-phenylbutanoicacid;N-BOC-D-HOMOPHENYLALANINE;N-Boc-D-Homophe-OH;(R)-2-(Boc-amino)-4-phenylbutyricacid;D-Homophenylalanine,N-BOCprotected;AmbotzBAA1288;AC1MBSGS;PubChem14954;BOC-D-HPHE;BOC-D-HPH;BOC-D-HPHE-OH;BOC-D-HFE-OH;BOC-D-HPH-OH;Boc-(D)-homophenylalanine;AC1Q1MU3;Boc-(D)-homo-phenylalanine;BOC-D-HOMOPHENYL-ALA;(R)-2-(TERT-BUTOXYCARBONYLAMINO)-4-PHENYLBUTANOICACID;15043_ALDRICH
Boc-D-homoPhenylalanine is a D-configured, non-proteinogenic amino acid building block featuring an extended side chain terminating in a phenyl group, supplied as the Nα-Boc protected derivative for controlled peptide coupling. Its stereochemistry and protected amino functionality make it a common choice for constructing stereochemically defined peptides and peptidomimetic segments where side-chain length and hydrophobic aromatic character are tuned. The Boc group supports standard protected-amino-acid workflows used in peptide intermediate preparation and stepwise assembly.
1. Stereodefined Peptide Building
Boc-D-homoPhenylalanine is used by peptide chemists to introduce a D-amino acid residue with an extended aliphatic spacer to a terminal phenyl ring, enabling precise control of backbone stereochemistry and side-chain topology in custom peptide synthesis. This makes it particularly relevant for producing stereochemically defined analogs for structure-activity relationship studies, where D-configuration and increased side-chain length can shift conformational preferences and proteolytic stability profiles in downstream assays. The Nα-Boc protection supports routine stepwise assembly into peptide intermediates and final peptide products using protected amino acid coupling strategies.
2. Peptidomimetic And SAR Studies
Boc-D-homoPhenylalanine supports medicinal chemistry research programs that develop peptidomimetics and non-natural peptide analogs by providing an aromatic, hydrophobic side chain with an extra methylene unit relative to phenylalanine. Researchers use this building block to probe how side-chain extension affects binding-site geometry, local hydrophobic interactions, and overall scaffold shape in SAR campaigns. Because it is supplied as a protected, stereochemically defined amino acid, it integrates cleanly into iterative synthesis of analog libraries where consistent residue identity is essential for meaningful structure-property comparisons.
3. Protected Amino Acid Intermediate Synthesis
Boc-D-homoPhenylalanine is also employed in the preparation of peptide fragments and protected intermediate sequences, where controlled deprotection and coupling steps require robust N-terminal protection. Custom peptide manufacturing workflows and academic peptide synthesis groups rely on Boc-protected amino acids to manage compatibility across multi-step assembly, especially when incorporating non-standard residues that must be introduced as discrete, well-defined units. The combination of D-configuration, Boc protection, and the homo-phenylalanine side chain makes it a practical reagent for building complex peptide intermediates used in subsequent purification and final product generation.
4. Non-Natural Residue Incorporation
Boc-D-homoPhenylalanine is frequently selected for the incorporation of non-natural amino acid features into peptide scaffolds, including both stereochemical inversion (D-configuration) and side-chain length expansion (homo-phenylalanine). Chemical biology and protein engineering teams use such residues to create tailored peptide segments for probing structure, function, and interaction modes in well-defined constructs. In these workflows, the protected form helps maintain synthetic fidelity during fragment assembly, ensuring that the intended residue identity is preserved through purification and downstream conjugation or assay preparation steps.
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