Cbz-2,5-Dimethy-L-Phenylalanine is a Cbz-protected, L-phenylalanine-derived amino acid bearing two methyl substituents at the 2 and 5 positions of the aromatic ring, placing it within the class of non-natural, sterically modified aromatic amino acids used for peptide and structure-activity studies. The molecule contains a free carboxyl group and an N-terminus protected as a benzyloxycarbonyl (Cbz) carbamate, while the side chain is a substituted benzyl group that provides hydrophobic/aromatic character and altered steric and electronic properties relative to phenylalanine. In synthesis, the Cbz protection supports chemoselective handling of the amino functionality during stepwise peptide assembly, and the modified aromatic substitution pattern provides a handle for incorporating this residue into peptides or for preparing labeled and analog series in binding and conformational analyses.
CAT No: CP14008
Cbz-2,5-Dimethy-L-Phenylalanine is a Cbz-protected, L-configured phenylalanine derivative bearing two methyl substituents at the 2- and 5-positions relative to the amino acid framework, creating a sterically defined chiral amino acid intermediate. The molecule contains a benzyloxycarbonyl (Cbz) carbamate on the amino group, a carboxylic acid functionality suitable for activation, and an aromatic side chain that provides hydrophobic and π-interaction features for peptide and peptidomimetic design. The combination of an aromatic ring with additional methyl substitution modulates conformational preferences and can influence coupling reactivity and downstream functionalization outcomes. The protected amine and defined stereocenter make it compatible with peptide coupling chemistries and protecting-group strategies that rely on orthogonal deprotection and controlled side-chain chemistry.
1. Peptide Synthesis
Cbz-2,5-Dimethy-L-Phenylalanine supports peptide building block preparation where the Cbz-protected amine participates as an N-terminal residue after activation of the carboxyl group. The L-configuration at the α-carbon and the substituted aromatic side chain enable incorporation into linear peptides and peptide fragments, allowing stereochemically defined backbone presentation. Cbz protection can be retained through coupling steps and removed under hydrogenolysis conditions when a free amine is required for subsequent elongation or cyclization. The resulting peptidic products can be used to probe sequence-dependent conformations and to generate analog libraries for structure-activity relationship studies in peptide science.
2. Side-Chain Functionalization
Cbz-2,5-Dimethy-L-Phenylalanine is suitable for amino acid derivatization workflows that exploit the aromatic ring and the sterically tuned side chain for controlled chemical modification. The carboxylic acid can be converted into activated intermediates for further transformations, while the Cbz carbamate provides a stable handle that can be selectively removed to expose an amine for conjugation or additional derivatization. The 2,5-dimethyl substitution pattern on the phenyl ring can affect electrophilic aromatic substitution, oxidative functionalization, and cross-coupling reactivity patterns used to introduce substituents for binding-site mapping. Downstream products may include functionalized peptide analogs and labeled amino acid derivatives used in biochemical research and synthetic organic chemistry.
3. Peptidomimetics And SAR
Cbz-2,5-Dimethy-L-Phenylalanine can be applied in peptidomimetic construction and structure-activity relationship studies where aromatic hydrophobicity and steric bulk are tuned to influence binding and conformational behavior. The protected amino acid format facilitates incorporation into constrained scaffolds, including cyclic peptides and backbone-modified analogs, while preserving stereochemical fidelity at the α-center. Cbz protection enables stepwise assembly strategies that separate amide bond formation from later amine-unmasking steps required for scaffold elaboration. The substituted phenyl side chain can serve as a definable pharmacophore element in SAR-driven library synthesis, supporting systematic variation of steric and electronic properties across analog series.
4. Pharmaceutical Intermediate Preparation
Cbz-2,5-Dimethy-L-Phenylalanine is relevant to pharmaceutical intermediate preparation and specialty chemical production where protected amino acid building blocks are manufactured for downstream medicinal chemistry programs. The Cbz carbamate and carboxylic acid functionality align with standard protected-amino-acid handling, enabling conversion to peptide coupling-ready derivatives and controlled deprotection sequencing during synthesis planning. The chiral L-stereocenter and substituted aromatic ring support manufacturing routes that require stereodefined intermediates for consistent impurity profiles and reproducible scaffold assembly. Industrially, the compound can be used as a chiral amino acid intermediate feeding fine chemical synthesis of peptide-like motifs and substituted aromatic amino acid derivatives.
5. Chemical Biology Bioconjugation
Cbz-2,5-Dimethy-L-Phenylalanine supports chemical biology and bioconjugation strategies that require defined amino acid residues for attaching biomolecular probes or constructing labeling handles. The Cbz-protected amine can be deprotected to generate a primary amine for coupling to activated esters, isothiocyanates, or other electrophiles used in probe attachment workflows. The aromatic, dimethyl-substituted side chain can contribute hydrophobic and π-interaction characteristics that influence conjugate solubility and local microenvironment effects in labeling constructs. The resulting amino acid-derived conjugates can be incorporated into peptide tags, affinity probes, or molecular recognition reagents used for biochemical investigation and analytical research.
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