Cbz-3-Methoxy-L-Phenylalanine is a Cbz-protected, L-configured phenylalanine derivative featuring a phenyl side chain bearing a meta (3-) methoxy substituent, classifying it as a substituted aromatic amino acid used as a peptide-building block. The molecule contains a free carboxylic acid and an N-terminal carbobenzyloxy (Cbz) protecting group, with the side-chain methoxy functionality providing an electron-donating aromatic substituent while the amino group is masked to control chemoselectivity during coupling. In peptide synthesis workflows, this protected amino acid is employed as a substrate for stepwise assembly of amide bonds, where the Cbz group helps prevent undesired side reactions of the amino functionality and the 3-methoxy aromatic side chain supports structure-activity and labeling studies of modified peptide analogues.
CAT No: CP15408
Cbz-3-Methoxy-L-Phenylalanine is a Cbz-protected L-phenylalanine derivative featuring a benzyloxycarbonyl (Cbz) group on the amino function and a 3-methoxy substituent on the aromatic side chain. The molecule retains the chiral α-carbon characteristic of L-phenylalanine, providing stereochemical control for peptide coupling and downstream stereodefinable transformations. The aromatic methoxy group modulates electronic density and can participate in electrophilic aromatic substitution, while the Cbz carbamate can be removed under hydrogenolysis-compatible conditions to regenerate the free amine for sequential synthesis. As an amino acid ester-free, N-protected aromatic building block, it functions as a stable chiral intermediate for protected amino acid chemistry and for constructing peptide and peptidomimetic frameworks with defined side-chain substitution patterns.
1. Peptide Synthesis
Cbz-3-Methoxy-L-Phenylalanine supports peptide building workflows in solid-phase or solution-phase peptide synthesis where an N-protected aromatic residue is required. The Cbz carbamate protects the α-amino group during coupling, while the L-configuration at the stereocenter ensures that the residue is incorporated with the intended stereochemical identity. The side-chain 3-methoxyphenyl group provides an aromatic handle that can influence local hydrophobicity and potential π-interactions in the growing sequence. Cbz-3-Methoxy-L-Phenylalanine can be used as a defined amino acid building block for generating peptide analogs, including sequence variants for biochemical assays and structure-activity relationship studies.
2. Side-Chain Functionalization
Cbz-3-Methoxy-L-Phenylalanine is suited to side-chain derivatization strategies that start from an anisole-type aromatic functionality. The 3-methoxy substituent can be retained for electronic tuning or transformed through demethylation to a phenol, enabling subsequent O-alkylation, acylation, or formation of aromatic ether/ester motifs. The protected amine remains masked during these transformations, reducing the likelihood of undesired amide or carbamate side reactions and preserving the amino acid scaffold for later coupling steps. Cbz-3-Methoxy-L-Phenylalanine therefore serves as a chiral intermediate for preparing functionalized aromatic amino acid derivatives and for assembling downstream conjugation-ready peptidomimetic fragments.
3. Chiral Amino Acid Intermediate
Cbz-3-Methoxy-L-Phenylalanine functions as a stereodefined chiral amino acid intermediate for synthetic organic chemistry routes that require an L-phenylalanine-derived stereocenter with controlled N-protection. The Cbz group provides a robust protecting-group platform compatible with many peptide-coupling and intermediate-manipulation conditions, while the aromatic methoxy substitution offers an additional site for selective functional group interconversions. The compound's defined stereochemistry enables predictable incorporation into larger molecules without racemization at the α-carbon when used as a residue precursor. Cbz-3-Methoxy-L-Phenylalanine can be applied to the preparation of protected amino acid derivatives, chiral fragments for fragment-based molecular design, and stereochemically consistent intermediates for fine chemical synthesis.
4. Bioconjugation Chemistry
Cbz-3-Methoxy-L-Phenylalanine can be used in chemical biology workflows that require aromatic amino acid motifs as conjugation handles within peptide-based probes. The protected α-amine allows sequential assembly into peptide carriers, after which Cbz removal can generate a free amine for further derivatization or for controlled attachment to activated linkers. The 3-methoxy aromatic side chain can be converted to a phenolic functionality when demethylation is performed, enabling attachment chemistries that rely on phenol reactivity or on subsequent formation of aromatic linkages. Cbz-3-Methoxy-L-Phenylalanine thus supports the construction of labeled peptide conjugates, biomolecule modification intermediates, and probe scaffolds used in binding studies and analytical method development.
5. Pharmaceutical Manufacturing Intermediates
Cbz-3-Methoxy-L-Phenylalanine is applicable to industrial peptide and peptidomimetic manufacturing where protected amino acid residues are processed through scalable coupling and protecting-group management. The Cbz-protected amine offers a practical protection strategy for controlling chemoselectivity during assembly of defined sequences or building blocks, while the L-stereocenter ensures stereochemical fidelity in the manufactured intermediate. The aromatic methoxy side chain can be used to tune solubility, aromatic content, and chemical reactivity profiles of the resulting peptide or fragment, supporting downstream formulation-relevant property control. Cbz-3-Methoxy-L-Phenylalanine can serve as a process chemistry intermediate for producing structured peptide fragments, SAR libraries, and manufacturing-grade peptidomimetic building blocks where consistent residue identity is required.
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