Cbz-2-Methoxy-L-Phenylalanine is a Cbz-protected, L-phenylalanine-derived amino acid bearing a 2-methoxy substituent on the aromatic ring, placing it in the class of substituted aromatic amino acids used as peptide-building blocks. The molecule contains an N-terminal benzyloxycarbonyl (Cbz) protecting group on the amino functionality and a free carboxylic acid, while the side chain features a methoxy-substituted phenyl group that can influence polarity and aromatic interactions. In peptide synthesis and structure-activity studies, this protected analogue is employed to introduce the 2-methoxyphenylalanine motif with controlled chemoselectivity during stepwise assembly and subsequent derivatization or analytical characterization of the resulting peptide or amino acid derivatives.
CAT No: CP15308
Cbz-2-Methoxy-L-Phenylalanine is an L-phenylalanine derivative bearing a benzyloxycarbonyl (Cbz) carbamate on the amino group and a 2-methoxy substituent on the aromatic ring. The molecule contains a stereogenic center at the alpha carbon, retaining the L-configuration that supports stereochemically defined peptide coupling and downstream chiral synthesis. The Cbz-protected amine and the aryl methoxy group together provide a controlled reactivity profile: the carbamate can be removed under hydrogenolysis conditions, while the anisole functionality can participate in electrophilic aromatic substitution or serve as a handle for further functional group interconversion. As a protected amino acid intermediate, it can be incorporated into peptide building block workflows or converted into C-terminal and side-chain modified analogs for structure-driven synthetic and biochemical studies.
1. Peptide Synthesis
Cbz-2-Methoxy-L-Phenylalanine is used in peptide synthesis as an N-Cbz protected amino acid building block that can undergo amide bond formation at the alpha carboxyl group while maintaining stereochemical integrity at the L-chiral center. The Cbz carbamate provides orthogonal protection relative to many side-chain and carboxyl activation strategies, enabling stepwise construction of peptide sequences using standard coupling chemistries. The 2-methoxyphenyl side chain introduces an electronically modulated aromatic motif that can influence conformational preferences and aromatic interactions in peptide analogs. Incorporation into short peptides, peptidomimetics, or protected fragment libraries supports downstream deprotection to reveal the free amine for sequential elongation and final assembly.
2. Side-Chain Functionalization
Cbz-2-Methoxy-L-Phenylalanine is applied in amino acid derivatization workflows where the aryl methoxy group acts as a functional handle for preparing substituted phenylalanine analogs. The anisole substituent can be transformed into other substituted aromatic functionalities through electrophilic aromatic substitution, demethylation to phenol, or further derivatization routes that preserve the L-amino acid stereocenter. The Cbz-protected amine supports selective chemistry by preventing undesired amide formation or side reactions during side-chain modification steps. Generated derivatives can be used to map side-chain effects in peptide structure-activity relationship studies, to build chemical biology probes, or to prepare substrate analogs for enzyme recognition studies.
3. Peptidomimetics And SAR Studies
Cbz-2-Methoxy-L-Phenylalanine is suitable for peptidomimetic construction and structure-activity relationship (SAR) studies that require defined aromatic substitution patterns on an amino acid scaffold. The combination of N-protection (Cbz) and the 2-methoxyphenyl side chain supports the synthesis of analog series where aromatic electronics and steric presentation are systematically varied while keeping the alpha stereochemistry constant. The protected amino acid form can be incorporated into constrained peptide-like frameworks or used as a fragment precursor for further functionalization, including conversion to alternative coupling-ready forms. Resulting analogs can serve as research reagents for studying binding-site preferences, aromatic interaction contributions, and stereochemical determinants in molecular recognition contexts.
4. Chemical Biology Probes
Cbz-2-Methoxy-L-Phenylalanine is used in chemical biology research to generate labeled or functionalized amino acid derivatives that can be installed into peptides or biomolecule conjugates. The Cbz-protected amine enables controlled deprotection to furnish a reactive primary amine for subsequent coupling steps, while the aromatic methoxy group can be retained to modulate hydrophobicity and electronic character in probe scaffolds. The L-configuration supports stereochemically defined incorporation into peptide sequences used for receptor studies, affinity reagents, or probe libraries. Downstream synthetic utility includes preparation of conjugation-ready intermediates and peptide analogs designed for imaging, pull-down chemistry, or mechanistic investigations of biomolecular interactions.
5. Pharmaceutical Intermediate Preparation
Cbz-2-Methoxy-L-Phenylalanine is employed as a chiral, protected amino acid intermediate in fine chemical synthesis routes that target peptide-derived active fragments and process-compatible building blocks. The Cbz carbamate provides a stable protecting-group strategy during manufacturing-relevant sequence assembly, while the aromatic methoxy substituent supports later conversion to other substituted phenyl motifs found in drug-like structures. The defined L-stereocenter and the presence of a carboxyl functionality enable conversion into coupling-ready intermediates for controlled amide formation in synthesis planning. Prepared downstream derivatives can feed into peptide-like scaffolds, stepwise synthesis of chiral intermediates, and intermediate supply chains for industrial-scale organic synthesis.
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