H-p-Bz-D-Phe-OH is a protected/unprotected amino acid derivative identified by a benzyl-type substituent on the aromatic ring and a free carboxylic acid, corresponding to a D-phenylalanine analogue bearing a p-benzyl (p-Bz) group on the side-chain phenyl ring. The molecule contains an amino group and a carboxyl group, with the aromatic side chain substituted at the para position, and it is specified in the D stereochemical form as indicated by the product name. This compound is used as a substrate building block in peptide and amino acid derivative synthesis and in structure-activity or labeling studies where an aromatic para-substituted phenylalanine residue is required for controlled steric and electronic effects.
CAT No: CP26714
CAS No:201466-03-7
Synonyms/Alias:201466-03-7;(R)-2-Amino-3-(4-benzoylphenyl)propanoicacid;D-4-Benzoylphenylalanine;4-Benzoyl-D-phenylalanine;AmbotzHAA5910;H-p-Bz-D-Phe-OH;H-D-BPA-OH;SCHEMBL288025;CTK8B4265;MolPort-003-795-015;ZINC2561081;0336AB;ANW-44554;AC-5873;CB-1297;AJ-40677;AK-90902;KB-209826;RT-009428;TL8001661;ST24026409;K-5898
H-p-Bz-D-Phe-OH is a D-phenylalanine carboxylic acid bearing an N-protecting benzyl-type group (p-benzyl) that preserves the stereochemical integrity of the D-amino acid center while masking the amino functionality for controlled peptide chemistry. The molecule contains an aromatic phenyl side chain characteristic of phenylalanine, along with a free carboxylic acid that can participate in amide-bond formation after activation. The N-protection strategy modulates nucleophilicity and reduces side reactions during coupling, while the chiral D-configuration enables stereochemically defined incorporation into peptide sequences and peptidomimetic scaffolds. The protected amino acid format also functions as a stable, isolable chiral intermediate for downstream transformations that require selective handling of the amino group versus the carboxyl group.
1. Peptide Synthesis
H-p-Bz-D-Phe-OH is used in peptide synthesis workflows where a D-phenylalanine residue is required for stereodefined peptide construction. The protected amino group supports controlled peptide coupling by allowing the carboxylic acid to be activated while the N-protection suppresses undesired oligomerization or side-chain acylation. The aromatic side chain can drive hydrophobic packing in peptide backbones and can be leveraged for generating D-amino acid-containing analogs that probe sequence effects. The resulting D-Phe incorporation supports the preparation of peptide building blocks for SPPS or solution-phase strategies and enables access to stereochemically pure peptide intermediates for subsequent deprotection and chain extension.
2. Peptidomimetics SAR Studies
H-p-Bz-D-Phe-OH serves as a chiral input for peptidomimetic construction in structure-activity relationship studies, where D-amino acid substitution is used to tune conformation and proteolytic stability. The D-configuration at the α-carbon provides stereochemical control over backbone geometry, while the phenyl side chain offers a defined hydrophobic/aromatic interaction handle for molecular recognition models. The N-protected amino acid form supports systematic derivatization into analog series by enabling selective coupling at the carboxyl functionality followed by orthogonal deprotection when required. Downstream scaffolds prepared from this intermediate can be used to generate SAR libraries that correlate stereochemistry and side-chain presentation with binding or functional readouts in biochemical assays.
3. Chemical Biology Probes
H-p-Bz-D-Phe-OH is applicable to chemical biology research requiring incorporation of D-phenylalanine into labeled peptides or biomolecule-targeting constructs. The protected amine and free carboxylic acid enable stepwise assembly of conjugatable peptide fragments, including the introduction of linkers or reactive handles at specific positions once the peptide segment is assembled. The aromatic side chain can be retained as a stable recognition element or used as a scaffold for further functionalization through side-chain-directed synthetic routes. The stereodefined D-amino acid residue helps maintain structural fidelity in probe design, supporting the synthesis of defined conjugates used for mechanistic studies and protein-interaction mapping.
4. Chiral Building Block Development
H-p-Bz-D-Phe-OH is suitable as a chiral amino acid intermediate for stereoselective synthesis of D-configured building blocks used in fine chemical and peptide-analog manufacturing. The molecule's N-protection strategy provides a controllable protecting-group platform that can be carried through coupling steps and then removed under conditions compatible with the carboxylic acid activation chemistry. The presence of a single stereogenic center and a nonpolar phenyl side chain simplifies route design for producing stereochemically consistent intermediate batches. The compound can be employed to access downstream derivatives such as activated esters, amide-linked fragments, or protected peptide segments that serve as intermediates in larger synthetic programs.
5. Pharmaceutical Intermediate Preparation
H-p-Bz-D-Phe-OH can be used in pharmaceutical intermediate preparation where D-amino acid residues are incorporated into peptide-like or constrained peptidomimetic structures during process development. The protected N-terminus reduces side reactions during coupling and supports reproducible assembly of defined fragments that later undergo functional group interconversions. The free carboxylic acid enables conversion to activated intermediates for controlled amide formation, supporting manufacturing-scale synthesis planning that relies on predictable chemoselectivity. The resulting D-Phe-containing intermediates can feed into downstream synthesis of drug-discovery candidates and process-relevant reference materials used for analytical method development and characterization.
6. Analytical Reference Standards
H-p-Bz-D-Phe-OH is applicable to analytical research as a stereochemically defined reference material for method validation and characterization of D-phenylalanine-containing peptide fragments. The combination of N-protection and carboxylic acid functionality provides a distinct, well-defined chemical signature that can be used to monitor coupling efficiency, deprotection outcomes, and impurity profiles in peptide synthesis and derivatization workflows. The aromatic phenyl group and the chiral center contribute to chromatographic and spectrometric distinguishability from L-analogues and other protected amino acids. The compound can therefore serve as an analytical standard and intermediate control point in quality-focused synthesis and characterization of amino acid derivatives and peptide building blocks.
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