Cbz-3,5-Dimethy-L-Phenylalanine is a Cbz-protected, L-phenylalanine-derived amino acid featuring a phenylalanine backbone with a 3,5-dimethyl substitution on the aromatic side chain. The molecule contains a free carboxyl group and an N-terminus masked as a benzyloxycarbonyl (Cbz) carbamate, while the side chain retains a hydrophobic, sterically hindered benzyl-like aromatic functionality that can influence peptide incorporation and conformational preferences. As a protected amino acid building block, it is used in peptide synthesis workflows to support chemoselective coupling at the carboxyl functionality while preventing undesired N-alkylation or side reactions associated with the amino group.
CAT No: CP14308
Cbz-3,5-Dimethy-L-Phenylalanine is an N-Cbz protected L-phenylalanine derivative bearing two methyl substituents on the aromatic ring at the 3 and 5 positions, creating a sterically differentiated, hydrophobic side chain. The structure combines a benzyloxycarbonyl (Cbz) carbamate on the amino group with a free carboxyl functionality, enabling controlled peptide coupling while preserving the chiral configuration of the α-carbon. Aromatic ring dimethylation modulates conformational preferences, increases lipophilicity, and can influence aromatic-aromatic and hydrophobic contacts in peptide and peptidomimetic scaffolds. The N-protecting Cbz group supports standard deprotection strategies during protected amino acid synthesis, while the amino acid framework serves as a chiral intermediate for downstream functionalization and peptide construction.
1. Peptide Synthesis
Cbz-3,5-Dimethy-L-Phenylalanine is applied in peptide building-block preparation where N-Cbz protection and the L-configuration support stepwise amide bond formation. The carboxylic acid and carbamate-protected amine allow peptide coupling chemistry while the 3,5-dimethylphenyl side chain can be used to tune hydrophobic packing and steric shielding in the growing chain. Cbz protection can be removed under conditions compatible with many peptide synthesis workflows, enabling sequential incorporation into longer sequences. The resulting peptide analogs can be used as research-grade substrates for studying backbone-side-chain effects and as intermediates toward peptidomimetic designs.
2. Side-Chain Functionalization
Cbz-3,5-Dimethy-L-Phenylalanine is suitable for amino acid derivatization strategies that exploit the substituted aromatic ring as a handle for further synthetic elaboration. The 3,5-dimethyl substitution pattern can direct electrophilic aromatic substitution, cross-coupling, or oxidative functional group installation on the phenyl ring after Cbz deprotection or side-chain exposure. The preserved chiral center and amino acid backbone maintain stereochemical integrity through multi-step transformations, supporting the construction of chiral side-chain-modified derivatives. Downstream products may include aromatic-functional peptidomimetics and protected intermediates used for structure-activity relationship studies in molecular design programs.
3. Chiral Amino Acid Intermediate
Cbz-3,5-Dimethy-L-Phenylalanine functions as a chiral amino acid intermediate for stereoselective synthesis of substituted phenylalanine motifs in fine chemical production. The L-α-amino acid framework with an N-Cbz carbamate provides a stable, isolable form that can be carried through protection, coupling, and deprotection steps without racemization under appropriately controlled conditions. The aromatic dimethyl pattern introduces defined steric and electronic characteristics that can be propagated into downstream chiral intermediates, including protected amino acids for fragment assembly. This makes the compound applicable to process chemistry routes where consistent stereochemistry and protected-group compatibility are required for reliable peptide building-block manufacturing.
4. Peptidomimetics And SAR Studies
Cbz-3,5-Dimethy-L-Phenylalanine is used in peptidomimetic construction where a substituted phenylalanine residue can modulate binding pocket hydrophobicity and steric complementarity. The N-Cbz group enables incorporation into peptide-like backbones, while the 3,5-dimethylphenyl side chain can influence conformational preferences and aromatic contact patterns in structure-activity relationship studies. The compound's protected amino acid form supports systematic analog generation by varying neighboring residues while keeping the stereogenic center fixed. Resulting analog libraries and single-residue substitution studies can be applied to biochemical research programs that probe molecular recognition and sequence-dependent structure effects.
5. Pharmaceutical Manufacturing Intermediates
Cbz-3,5-Dimethy-L-Phenylalanine is relevant to pharmaceutical intermediate preparation where controlled protection of the amino functionality supports scalable peptide coupling chemistry. The Cbz carbamate and free carboxyl functionality align with industrially established protected amino acid strategies, enabling consistent handling during multi-step syntheses and purification workflows. The substituted aromatic side chain can serve as a defined component in manufacturing routes for peptide-based or peptide-derived intermediates used in specialty chemical production. Downstream processing can incorporate this residue into larger protected fragments, supporting reproducible generation of chiral building blocks for regulated chemical manufacturing pipelines.
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