Boc-L-beta-HPhe-OH is a protected amino acid derivative in which the amino group of L-β-homophenylalanine is carbamated with a Boc (tert-butoxycarbonyl) group, yielding a β-substituted phenylalanine scaffold. The molecule contains both an N-Boc-protected amino functionality and a free carboxylic acid, with a β-position side chain bearing an additional phenyl substituent that increases hydrophobic character and provides a defined aromatic handle for peptide and structure-activity studies. As a Boc-protected building block, it is used in peptide synthesis workflows to control chemoselectivity at the amine during stepwise coupling and to generate β-substituted aromatic residues in unnatural and modified peptide analogues.
CAT No: CP25871
CAS No:51871-62-6
Synonyms/Alias:(S)-3-(Boc-amino)-4-phenylbutyricacid;51871-62-6;Boc-L-beta-homophenylalanine;Boc-beta-Homophe-OH;(3S)-3-[(tert-butoxycarbonyl)amino]-4-phenylbutanoicacid;PubChem12107;AC1MC56G;Boc-L-|A-homophenylalanine;TMBA023;14979_ALDRICH;SCHEMBL1519945;14979_FLUKA;CTK8C5210;MolPort-002-344-094;ZINC2572720;(3S)-N-Boc-3-Benzyl-beta-alanine;ANW-74675;MFCD01076271;SBB063813;AKOS015836515;AKOS015889772;BL730-1;AJ-42081;AK-35445;AM001932
Chemical Name:N-beta-(t-Butyloxycarbonyl)-L-Homophenylalanine
Boc-L-beta-HPhe-OH is a Boc-protected, β-substituted phenylalanine derivative designed for peptide and peptidomimetic synthesis where backbone substitution at the β-position is used to tune conformational behavior and chemical stability. The free carboxylic acid enables downstream coupling into peptide chains, while the Boc group provides an established strategy for controlled N-terminus reactivity during fragment assembly and purification workflows. As a chiral, amino-acid building block, it is commonly selected when researchers need a β-hydroxylated phenylalanine motif as a defined stereochemical element in modified peptides.
1. Peptide Backbone Modification
Boc-L-beta-HPhe-OH is used by peptide chemists to incorporate a β-hydroxylated phenylalanine residue into custom peptides and peptidomimetics, enabling systematic structure-property studies of backbone substitution effects. The β-hydroxy functionality provides a handle for later derivatization or for modulating hydrogen-bonding patterns within the peptide scaffold, while the Boc-protected amine supports controlled segment coupling in multi-step synthesis. This building block is particularly relevant for researchers assembling modified peptide libraries where defined stereochemistry at the β-position is required to compare analogs under consistent synthetic conditions.
2. Peptidomimetic SAR Intermediates
Boc-L-beta-HPhe-OH serves as a practical intermediate for medicinal chemistry programs that develop peptidomimetic or constrained peptide-like structures for structure-activity relationship (SAR) exploration. By embedding the β-hydroxy phenylalanine motif at a specific position, teams can probe how altered backbone polarity and local conformational preferences influence the behavior of peptide-derived scaffolds in downstream assays. The Boc-protected form and free acid functionality make it a convenient, isolable unit for building larger fragments that are later converted into fully assembled analogs for SAR workflows.
3. Modified Residue Segment Coupling
Boc-L-beta-HPhe-OH is frequently selected for segment condensation strategies in solution-phase or protected-fragment peptide synthesis, where a single, well-defined amino acid unit must be coupled with reproducible reactivity and stereochemical integrity. The combination of Boc protection on the amino group and a carboxylic acid at the α-position supports its use as a residue-level building block within larger peptide assemblies, including analogs that require careful control of functional-group compatibility during purification. Researchers commonly use this type of β-substituted amino acid building block to prepare peptides with non-standard backbones while maintaining a modular synthesis approach for rapid analog generation.
4. Functional Handle Derivatization
Boc-L-beta-HPhe-OH is also used in workflows that require subsequent functionalization of the β-hydroxyl group after peptide assembly or during fragment elaboration. The presence of the β-hydroxy moiety enables later conversion to protected or activated derivatives depending on the target application, supporting the preparation of peptide conjugation-ready intermediates and chemical biology tools derived from modified peptide backbones. This makes the building block valuable for teams designing peptide constructs where a defined polar substituent must be carried through synthesis and then transformed into a downstream reactive or compatibility-tuned functionality.
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