Cbz-2,4-Dimethy-L-Phenylalanine is a Cbz-protected, substituted phenylalanine derivative bearing a phenylalanine backbone with 2,4-dimethyl substitution on the aromatic ring and an L-stereochemical configuration as indicated by the product name. The molecule contains a carboxylic acid functionality masked as appropriate for a protected amino acid building block and an N-terminus protected by a benzyloxycarbonyl (Cbz) group, while the side chain features a hydrophobic aromatic ring with two additional methyl groups that modulate steric and packing characteristics. In peptide chemistry, this protected amino acid is used as a substrate for stepwise assembly of peptides or peptide analogues, where the Cbz group supports chemoselective handling of the amino functionality and the substituted aromatic side chain enables structure-activity and conformational studies.
CAT No: CP13908
Cbz-2,4-Dimethy-L-Phenylalanine is a Cbz-protected L-phenylalanine derivative bearing methyl substituents at the 2- and 4-positions of the aromatic ring, creating a defined chiral amino acid framework for stereocontrolled peptide chemistry. The molecule contains a benzyloxycarbonyl (Cbz) carbamate on the amino group and a free carboxylic acid functionality, enabling standard amino acid coupling while supporting orthogonal protection logic during multi-step synthesis. Aromatic ring methylation modulates electronic density and steric profile, which can influence coupling rates, side reactions, and subsequent derivatization of the phenyl side chain. As a chiral building block, Cbz-2,4-Dimethy-L-Phenylalanine functions as a protected amino acid intermediate for constructing substituted phenylalanine motifs used in peptide analogs, SAR-focused libraries, and downstream fine chemical transformations.
1. Peptide Synthesis
Cbz-2,4-Dimethy-L-Phenylalanine is suitable for peptide building-block workflows in solid-phase or solution-phase peptide synthesis, where the Cbz-protected amino group and carboxylic acid enable controlled amide bond formation. The L-configuration at the amino acid stereocenter supports stereochemically consistent incorporation into peptide backbones, while the 2,4-dimethylphenyl side chain provides a hydrophobic, sterically tuned residue for mimicking substituted aromatic pharmacophores. Cbz protection supports orthogonal deprotection strategies that can be aligned with other protecting groups used in peptide assembly, allowing sequential coupling and selective unveiling of the amine. The resulting peptide products can serve as substrate scaffolds for biochemical characterization, structure-activity relationship studies, and peptidomimetic optimization where aromatic substitution patterns are chemically encoded by the side chain.
2. Side-Chain Functionalization
Cbz-2,4-Dimethy-L-Phenylalanine is applied in synthetic organic chemistry and medicinal chemistry intermediate preparation where the substituted aromatic ring can be leveraged for subsequent functional group installation. The methylated phenyl side chain can direct electrophilic and radical transformations on the aromatic system, while the amino acid core remains protected at the N-terminus to preserve chemoselectivity during side-chain derivatization steps. The free carboxylic acid allows conversion to activated esters or coupling-ready forms when the compound is used as a precursor for mixed derivatives, including amide-linked aromatic analogs. Downstream products can include substituted aromatic peptide fragments, chiral intermediates for library synthesis, and chemically defined fragments for fragment-based molecular design workflows that require a specific stereochemical amino acid handle.
3. SAR Studies
Cbz-2,4-Dimethy-L-Phenylalanine is used in structure-activity relationship studies and molecular design programs to introduce a defined substituted phenylalanine residue into peptide-like scaffolds. The combination of the Cbz-protected amine and the carboxylic acid supports standardized peptide coupling chemistry, enabling systematic variation of aromatic substitution while holding the backbone stereochemistry constant. The 2,4-dimethyl substitution pattern modulates aromatic hydrophobicity and steric bulk, which can be encoded into analog series to probe binding pocket tolerance and conformational preferences in peptide analogs. The compound therefore serves as a chiral, structure-defined intermediate for generating SAR panels and comparative analogs where side-chain electronics and sterics are varied through amino acid derivatization rather than backbone alteration.
4. Protected Amino Acid Chemistry
Cbz-2,4-Dimethy-L-Phenylalanine is employed as a protected amino acid derivative in synthetic route design requiring N-protection compatible with peptide coupling and controlled deprotection sequencing. The Cbz carbamate provides a stable N-protected handle during activation of the carboxyl group and formation of amide bonds, while the L stereocenter supports stereochemical fidelity across multi-step syntheses. The presence of a free carboxylic acid enables conversion to coupling reagents or protected acid derivatives as needed for orthogonal strategies in complex intermediate assembly. This makes the compound a practical chiral amino acid intermediate for fine chemical synthesis where protected amino acid chemistry, orthogonal protection planning, and downstream fragment generation are central to manufacturing-scale feasibility.
5. Pharmaceutical Manufacturing
Cbz-2,4-Dimethy-L-Phenylalanine is relevant to pharmaceutical manufacturing and specialty chemical production pipelines that require reproducible incorporation of substituted amino acid residues into peptide intermediates. The Cbz-protected amino group and carboxylic acid functionality support robust, scalable peptide coupling chemistries used to generate defined peptide fragments or peptidomimetic intermediates for further processing. The aromatic methyl substituents can influence solubility and crystallization behavior of downstream intermediates, which can be important for process design and intermediate isolation planning. The compound's role as a chiral, protected amino acid building block aligns with industrial fine chemical synthesis needs for consistent stereochemical outcomes and predictable functional group reactivity during intermediate preparation.
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