Cbz-3-Methy-L-Phenylalanine is a Cbz-protected, L-phenylalanine-derived amino acid derivative bearing a phenyl side chain substituted with a 3-methyl group, classifying it as a substituted aromatic amino acid for peptide chemistry. The molecule contains an N-Cbz carbobenzyloxy protecting group on the amino functionality and an unprotected carboxylic acid for coupling, with the side chain presenting a hydrophobic aromatic surface and the stereocenter specified as L in the product name. In synthesis, it functions as a protected building block for stepwise peptide assembly where the Cbz group controls chemoselectivity of the amino functionality while the free carboxyl group enables formation of amide bonds in peptide and peptidomimetic intermediate preparation.
CAT No: CP15708
Cbz-3-Methy-L-Phenylalanine is a Cbz-protected, chiral phenylalanine derivative in which the side chain bears an additional methyl substituent at the 3-position of the aromatic ring (3-methyl-L-phenylalanine framework). The molecule contains a benzyloxycarbonyl (Cbz) carbamate on the amino group and a free carboxyl functionality or carboxyl-derivative state depending on the supplied form, enabling controlled peptide coupling and subsequent deprotection chemistry. The stereogenic center at the alpha carbon is set to the L-configuration, supporting stereospecific incorporation into peptide sequences and chiral SAR scaffolds. The aromatic ring with a methyl substituent modulates hydrophobicity and steric profile, while the Cbz protecting group provides stability under peptide coupling conditions and can be removed to regenerate the reactive amine for further transformations.
1. Peptide Synthesis
Cbz-3-Methy-L-Phenylalanine is used as a protected amino acid building block for solid-phase or solution-phase peptide synthesis where an N-Cbz carbamate supports reliable amide bond formation. The Cbz group protects the alpha-amino functionality from side reactions during coupling, while the L-configured alpha stereocenter enables stereochemically consistent peptide assembly. The aromatic side chain bearing a 3-methyl substituent participates in hydrophobic packing and can tune local conformational preferences in peptide analogs. Downstream, deprotection of the Cbz group can regenerate the amine for iterative coupling steps or for post-synthetic functionalization, supporting routine peptide construction and protected amino acid synthesis workflows.
2. Peptidomimetics And SAR Studies
Cbz-3-Methy-L-Phenylalanine is applied in peptidomimetic and structure-activity relationship studies where aromatic side-chain substitution is used to modulate binding interactions. The methyl-substituted phenyl ring provides a controlled change in steric bulk and lipophilicity relative to unsubstituted phenylalanine, which can be leveraged during molecular design of constrained or analog peptide scaffolds. The Cbz-protected amine and chiral backbone facilitate incorporation into peptide-like frameworks while maintaining compatibility with standard peptide coupling and protecting-group strategies. The resulting analogs can serve as focused SAR intermediates for generating libraries of aromatic variants and for mapping structure-function relationships in amino acid-derived chemical biology probes.
3. Side-Chain Functionalization
Cbz-3-Methy-L-Phenylalanine is suitable for side-chain derivatization routes that start from an aromatic amino acid scaffold bearing a methyl-substituted phenyl group. The Cbz carbamate stabilizes the alpha-amino functionality during electrophilic aromatic manipulation, oxidation-state adjustments, or further derivatization steps that target the aromatic ring or nearby substituents. The preserved stereocenter allows the compound to act as a chiral intermediate while functional groups introduced onto the aromatic system can be carried into peptides or small molecules. Downstream products can include modified aromatic residues for tuning hydrophobic contacts, enabling access to substituted phenylalanine derivatives used in synthetic organic chemistry and peptide science.
4. Chemical Biology Probes
Cbz-3-Methy-L-Phenylalanine can be employed in chemical biology research to generate amino acid-based probes and peptide-tagged constructs for studying biomolecular interactions. The protected amino acid format supports stepwise incorporation into peptides that carry reactive handles elsewhere in the sequence, while the 3-methyl phenyl side chain contributes to noncovalent recognition through hydrophobic and aromatic interactions. The Cbz group allows controlled deprotection to expose the amine when assembling conjugation-ready intermediates, including sequences designed for subsequent labeling or immobilization. The chiral L-configuration helps maintain stereospecific behavior in peptide-based probes, supporting downstream formation of functionalized biomolecule-interaction reagents.
5. Pharmaceutical Intermediate Preparation
Cbz-3-Methy-L-Phenylalanine is used as a chiral intermediate in fine chemical and pharmaceutical intermediate preparation where protected amino acid derivatives are required for controlled synthesis of peptide-like or aromatic-containing fragments. The N-Cbz protection strategy supports manufacturing-compatible protection/deprotection logic, allowing the amine to remain masked during coupling steps and to be unmasked for subsequent transformations. The methyl-substituted phenylalanine motif can serve as a defined stereochemical and structural element in drug discovery chemistry, including synthesis of modified amino acid residues for lead optimization. Downstream, the compound can feed into larger intermediate assemblies, enabling consistent stereochemical incorporation into complex molecules and supporting process chemistry intermediate generation based on amino acid chemistry principles.
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