Boc-D-beta-HPhe-OH is a protected amino acid derivative featuring a Boc-protected amino group on the alpha-amino position of a D-configured β-homologated phenylalanine analog (β-homophenylalanine). The molecule contains a free carboxylic acid (-COOH) and a β-substituted side chain bearing a phenyl group, with the Boc group serving as an amino protecting group that controls chemoselectivity by suppressing undesired side reactions at the nitrogen during peptide-coupling steps. As a building block for peptide and peptidomimetic synthesis, it is employed in stepwise assembly strategies where the extended β-carbon spacing and protected amine enable incorporation of this β-substituted aromatic residue into larger amino acid and peptide frameworks.
CAT No: CP25114
CAS No:101555-61-7
Synonyms/Alias:boc-d-beta-homophenylalanine;101555-61-7;(R)-3-tert-Butoxycarbonylamino-4-phenyl-butyricacid;(r)-3-(tert-butoxycarbonylamino)-4-phenylbutanoicacid;(R)-3-Boc-amino-4-phenylbutyricacid;boc-(r)-3-amino-4-phenylbutyricacid;boc-d-beta-hophe-oh;AmbotzBAA6100;PubChem18642;Boc-beta-D-Homophe-OH;boc-d-phe-(c*ch2)oh;AC1ODVM4;(r)-boc-b2-homophenylalanine;SCHEMBL489489;CTK8E2809;ACKWQHCPHJQANL-GFCCVEGCSA-N;MolPort-000-001-458;ZINC2572719;CB-717;AN-7395;(r)-3-boc-amino-4-phenyl-butyricacid;AJ-42080;AK-90330;Q525;AB0017643
Chemical Name:N-beta-(t-Butyloxycarbonyl)-D-homophenylalanine
Boc-D-beta-HPhe-OH is a Boc-protected D-configured β-homophenylalanine amino acid derivative designed for peptide and peptidomimetic synthesis. The extended β-carbon side chain relative to phenylalanine provides an additional methylene unit that can be used to tune backbone geometry and side-chain spacing in sequence-defined constructs. As a protected amino acid building block, it is commonly handled as a stable intermediate for controlled incorporation into protected peptide segments during synthetic assembly.
1. Peptide Synthesis Building Block
Boc-D-beta-HPhe-OH is widely used by peptide chemistry groups to incorporate D-β-homophenylalanine into peptide sequences where stereochemical inversion and altered side-chain reach are strategically important. The Boc-protected amino functionality supports downstream coupling strategies in protected-segment workflows, enabling consistent assembly of peptides and peptidomimetics with defined stereochemistry at the α-carbon. Researchers often select the β-homophenylalanine scaffold to adjust local conformations, improve resistance to proteolytic cleavage in peptide-like systems, or probe structure-activity relationships by systematically varying side-chain topology.
2. Peptidomimetic And SAR Studies
Boc-D-beta-HPhe-OH is frequently chosen in medicinal chemistry and chemical biology programs building peptidomimetics for structure-activity relationship (SAR) investigations. The β-homolog phenylalanine side chain changes the spatial relationship between aromatic functionality and the peptide backbone, which can be leveraged to map how side-chain length and stereochemistry influence binding-site geometry in receptor- or enzyme-focused assays. Using the D configuration allows researchers to explore stereochemical effects while maintaining a chemically well-defined amino acid building block for parallel library synthesis and comparative evaluation.
3. Protected Segment Intermediate Development
Boc-D-beta-HPhe-OH serves as a practical protected amino acid intermediate for preparing defined peptide segments used in custom peptide manufacturing and academic synthesis campaigns. The Boc protection pattern supports its handling as a discrete building block that can be incorporated into larger protected sequences with controlled functional-group compatibility. This makes it useful when developing multi-step synthetic routes to complex peptides where reliable incorporation of a β-substituted, stereodefined residue is required for consistent downstream purification and characterization of the final product.
4. Chiral Amino Acid Derivative Synthesis
Boc-D-beta-HPhe-OH is also used in chiral intermediate development workflows where D-β-homophenylalanine derivatives are required as stereochemically defined starting materials. Synthetic chemistry teams employ this building block to access β-homolog aromatic amino acid motifs for further functionalization or for preparing analog series that differ in side-chain length, stereochemistry, or protected-group architecture. In these programs, the combination of D-configuration and Boc protection provides a convenient, reproducible entry point for constructing stereochemically controlled amino acid derivatives used in peptide-like materials and structure-guided chemical design.
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