Cbz-3,4-Dimethy-L-Phenylalanine is a Cbz-protected, substituted phenylalanine derivative bearing two methyl substituents on the aromatic ring at the 3- and 4-positions, classifying it as a non-natural, ring-modified amino acid suitable for peptide chemistry. The molecule contains an amino group and a carboxyl group in the amino-acid framework, with the amine masked as a benzyloxycarbonyl (Cbz) carbamate that moderates chemoselectivity during coupling, while the stereochemical descriptor "L" specifies the configuration at the α-carbon. In synthesis, the protected amino acid functions as a building block for stepwise peptide assembly and structure-activity studies where aryl substitution patterns and hydrophobicity of the side chain are varied, and it can also be used in chemical labeling or analytical workflows that require defined aromatic ring functionality.
CAT No: CP14208
Cbz-3,4-Dimethy-L-Phenylalanine is a chiral phenylalanine derivative bearing an N-Cbz (benzyloxycarbonyl) protecting group and a side chain substituted at the 3,4-positions with two methyl substituents on the aromatic ring. The molecule retains the amino acid stereocenter at the alpha-carbon (L-configuration), presenting a controlled chiral handle for stereoselective peptide coupling and downstream transformations. The Cbz carbamate masks the primary amine to suppress undesired side reactions during activation and coupling, while the aromatic ring with ortho/para-directed methyl groups modulates sterics and electronic properties relevant to aromatic stacking and hydrophobic interactions. The resulting protected amino acid intermediate is compatible with standard peptide synthesis logic and can be converted into functional derivatives after selective deprotection or side-chain functional group manipulation.
1. Peptide Synthesis
Cbz-3,4-Dimethy-L-Phenylalanine is used in peptide building workflows where an N-protected amino acid is required for controlled amide bond formation. The Cbz-protected amine and the free carboxyl functionality support coupling chemistries that build peptide chains while minimizing racemization at the L-alpha stereocenter. The substituted phenyl side chain introduces steric bulk and altered aromatic character, enabling incorporation of hydrophobic and shape-defined residues into peptide sequences and peptidomimetic scaffolds. Following assembly, Cbz removal can regenerate the reactive amine for sequential elongation or for generating defined peptide termini, supporting stepwise synthesis of complex peptide analogs.
2. Side-Chain Functionalization
Cbz-3,4-Dimethy-L-Phenylalanine is applicable to side-chain engineering strategies in synthetic organic chemistry and biochemical probe design. The 3,4-dimethyl-substituted aromatic ring provides a hydrophobic, sterically biased aryl motif that can participate in electrophilic aromatic substitution, directed functionalization, or oxidative/derivatization routes to introduce additional substituents on the aromatic scaffold. The N-Cbz protection helps maintain chemoselectivity during aromatic modification steps, allowing functional groups to be installed on the side chain without compromising the amino acid functionality. The resulting derivatives can be used to tune binding interactions, adjust lipophilicity, or generate handles for further conjugation chemistry in downstream molecular construction.
3. Peptidomimetics And SAR Studies
Cbz-3,4-Dimethy-L-Phenylalanine is suitable for structure-activity relationship studies that require systematic variation of aromatic residue properties within peptide-like frameworks. The L-configuration at the alpha-carbon preserves stereochemical fidelity, while the N-Cbz group enables incorporation as a protected building block into analog series without premature amine reactivity. The 3,4-dimethyl substitution pattern can modulate conformational preferences and aromatic contact surfaces, supporting rational comparison of analogs that differ in steric profile and hydrophobic character. Synthesized peptide analogs can then serve as research intermediates for mapping binding determinants and for generating libraries of analogs for medicinal chemistry and chemical biology investigations.
4. Chemical Biology Probes
Cbz-3,4-Dimethy-L-Phenylalanine is employed in chemical biology workflows where protected amino acid derivatives are used to build labeled or reactive biomolecule fragments. The carbamate-protected amine supports controlled incorporation into peptide tags, affinity handles, or recognition elements while maintaining stability under coupling conditions. The substituted phenylalanine side chain can function as a hydrophobic/aromatic anchor that influences localization, membrane association tendencies, or interaction with aromatic binding pockets in target proteins. After peptide assembly, Cbz deprotection and subsequent functional group installation can enable probe generation for downstream studies of protein interactions, substrate recognition, or biomolecular assembly processes.
5. Pharmaceutical Intermediate Preparation
Cbz-3,4-Dimethy-L-Phenylalanine is relevant to pharmaceutical intermediate preparation where defined chiral amino acid building blocks are required for manufacturing-grade peptide fragments and peptidomimetic intermediates. The N-Cbz protecting group provides a robust protection strategy for the amino functionality during activation, coupling, and intermediate handling steps typical of process chemistry. The stereochemically defined L-alpha center supports consistent incorporation into downstream sequences, while the substituted aromatic side chain can be carried through as a stable motif until later deprotection or conversion steps. The compound can therefore serve as a controlled chiral input for fine chemical synthesis routes that produce protected peptide segments, enabling reproducible downstream derivatization and intermediate generation for applied product development.
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