Cbz-D-homoPhenylalanine is a protected, non-proteinogenic amino acid derivative featuring a homo-extended phenylalanine side chain (β-phenylpropyl) and a stereochemical designation of D at the α-carbon. The molecule contains a free carboxyl group and an amino group masked as a benzyloxycarbonyl (Cbz) carbamate, which controls chemoselectivity during peptide coupling and suppresses undesired side reactions from the nitrogen. In synthetic peptide chemistry and structure-activity studies, it functions as a building block for introducing a D-configured, homo-phenylalanine residue into protected amino acid sequences or as a precursor to further amino acid and peptide derivatives.
CAT No: CP17411
CAS No:138812-70-1
Synonyms/Alias:138812-70-1;Cbz-D-homoPhenylalanine;Z-D-HOMOPHE-OH;(R)-2-(((Benzyloxy)carbonyl)amino)-4-phenylbutanoicacid;Cbz-D-Homophe;Cbz-D-Hph-OH;Z-D-homophenylalanine;Cbz-D-homophenyl-Ala;SCHEMBL1796250;BDBM36224;CTK8B7896;MolPort-003-990-187;ZINC2539576;ANW-58884;AKOS015911471;AM83540;AJ-38897;AK-58931;KB-48800;RT-016306;FT-0643300;V2882;K-4493;I14-37315;(2R)-2-{[(benzyloxy)carbonyl]amino}-4-phenylbutanoicacid
Cbz-D-homoPhenylalanine is a Cbz-protected D-configured amino acid derivative featuring a benzyloxycarbonyl (Cbz) carbamate on the stereogenic amino acid nitrogen and an extended homo-phenylalanine side chain with a terminal benzyl aromatic ring. The D-configuration at the alpha carbon provides defined stereochemistry for stereocontrolled peptide coupling and for preparing chiral amino acid building blocks used in unnatural amino acid incorporation. The molecule bears a carboxylic acid functionality suitable for conversion to activated esters or coupling partners, while the aromatic side chain can participate in hydrophobic, π-stacking, and aromatic interaction motifs in peptide and peptidomimetic scaffolds. The Cbz protecting group enables orthogonal deprotection strategies under hydrogenolysis conditions, supporting downstream peptide synthesis workflows and the construction of stereochemically defined oligomers.
1. Peptide Synthesis
Cbz-D-homoPhenylalanine supports peptide building block preparation by combining a protected amino terminus with a free carboxyl group that can be activated for amide bond formation. The D-stereocenter and the extended homo-phenylalanine side chain length influence backbone conformation and side-chain positioning during coupling, which is relevant for constructing peptides with defined stereochemical outcomes. The Cbz carbamate can be removed after chain assembly to reveal the amine for subsequent coupling steps or for generating terminal functional groups. Peptide synthesis compatibility makes the compound suitable for preparing D-amino acid-containing sequences and for generating peptide variants used in mechanistic studies and scaffold optimization.
2. Peptidomimetics And SAR
Cbz-D-homoPhenylalanine is applicable to peptidomimetic construction and structure-activity relationship studies where aromatic side-chain geometry and stereochemistry affect binding-site recognition. The homo-phenylalanine side chain provides an extra methylene relative to phenylalanine, enabling tuning of hydrophobic contact distance and aromatic interaction patterns in analog libraries. The D-configuration supports incorporation of conformationally constrained or protease-resistant motifs, while the Cbz group allows controlled stepwise assembly and later functional group unveiling. Downstream derivatives can be accessed through side-chain functionalization or by converting the carboxyl functionality into alternative coupling handles for SAR-focused analog generation.
3. Protected Amino Acid Chemistry
Cbz-D-homoPhenylalanine functions as a chiral, N-Cbz protected amino acid intermediate for protected amino acid synthesis and protecting-group strategy development. The Cbz carbamate provides a stable nitrogen protection handle during carboxyl activation and peptide coupling chemistry, while remaining compatible with orthogonal deprotection sequences that can be integrated into multi-step syntheses. The presence of a stereogenic center in the D-series supports stereochemically defined intermediate preparation for downstream chiral building blocks. The compound can be employed to access activated carboxyl derivatives, enabling systematic exploration of peptide coupling conditions and intermediate stability in fine chemical synthesis.
4. Chemical Biology Probes
Cbz-D-homoPhenylalanine can be used in chemical biology research for preparing amino acid-containing probes and labeled peptide fragments that track molecular interactions. The aromatic side chain provides a scaffold for hydrophobic and π-interaction-driven recognition, while the D-amino acid stereochemistry can modulate proteolytic stability of probe constructs. The Cbz-protected amine and carboxylic acid functionality support conversion into conjugation-ready intermediates, including activated carboxyl forms for attachment to linkers or reporter-bearing moieties. Resulting probe derivatives can serve as building blocks for studying binding interfaces, receptor interactions, or enzyme-substrate recognition using stereochemically defined amino acid patterns.
5. Pharmaceutical Intermediate Preparation
Cbz-D-homoPhenylalanine is suitable for pharmaceutical intermediate preparation where chiral amino acid derivatives are required for peptide-like ingredient synthesis and process chemistry routes. The protected amino group and carboxyl functionality enable manufacturing-compatible transformations into coupling-ready intermediates, including activated carboxyl derivatives used for amide formation. The D-homo-phenylalanine motif supports incorporation into non-natural peptide segments that may be used as intermediates toward larger functional molecules. The Cbz protecting group provides a controllable protection/deprotection element that can be integrated into stepwise synthetic sequences for producing stereochemically defined intermediates at scale.
6. Analytical Standards the
Cbz-D-homoPhenylalanine can be employed as an analytical reference material and method development standard for chiral amino acid analysis and peptide hydrolysate profiling. The D-configuration and N-Cbz protection create a distinct chromatographic and mass spectrometric signature, supporting identification of stereochemical incorporation in peptide building block studies. The aromatic side chain and protected nitrogen enable robust detection after controlled deprotection or derivatization workflows used in analytical research. Analytical use extends to verifying the integrity of protected amino acid intermediates and monitoring stereochemical outcomes in peptide coupling and deprotection sequences.
1. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
2. An Open-label, Single-center, Safety and Efficacy Study of Eyelash Polygrowth Factor Serum
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