Cbz-4-Methy-D-Phenylalanine is a Cbz-protected, non-natural amino acid derivative bearing a benzyl carbamate (Cbz) on the amino group and a carboxylic acid functionality, with a side chain that is a 4-methyl-substituted phenylalanine framework and a specified D stereochemical configuration at the alpha carbon. The molecule contains a free carboxyl group for coupling chemistry and a protected alpha-amino group that suppresses undesired amide formation during selective transformations, while the aromatic side chain provides hydrophobic character and a defined substitution pattern for studying structure-property relationships. In peptide chemistry and chemical biology workflows, it is used as a protected building block to incorporate the 4-methyl-substituted phenylalanine motif into peptide sequences or to prepare labeled and structurally modified amino acid/peptide intermediates for analytical method development and structure-activity studies.
CAT No: CP15809
Cbz-4-Methy-D-Phenylalanine is a chiral, N-Cbz-protected phenylalanine derivative bearing a D-stereocenter and a 4-methyl-substituted phenyl side chain. The molecule contains a carbobenzyloxy (Cbz) group on the amino nitrogen, a free carboxylic acid functionality or acid-reactive form depending on the supplier specification, and an aromatic side chain that contributes to hydrophobic and π-interaction character. The D-configuration at the α-carbon supports stereochemically defined peptide incorporation and can influence conformational preferences in peptide analogs. The Cbz protecting group provides stability under many coupling conditions while enabling controlled deprotection for subsequent peptide assembly or downstream derivatization.
1. Peptide Synthesis
Cbz-4-Methy-D-Phenylalanine is used as a stereodefined peptide building block in solid-phase or solution-phase peptide synthesis. The N-Cbz protection enables peptide coupling chemistries that require an unreactive amine during activation of the carboxyl group, while the aromatic side chain with a 4-methyl substituent can be used to tune hydrophobic packing and aromatic contact patterns in peptide sequences. D-configuration at the α-carbon supports incorporation of D-amino acid residues for generating protease-resistant peptide frameworks and for studying stereochemical effects on folding and binding. Controlled Cbz deprotection can then expose the amine for sequential chain extension, enabling stepwise construction of D-containing peptides and peptidomimetics.
2. Peptidomimetics And SAR Studies
Cbz-4-Methy-D-Phenylalanine is applied in peptidomimetic design and structure-activity relationship (SAR) studies where side-chain electronics and sterics are varied systematically. The 4-methyl-substituted phenyl group provides a handle for modulating aromatic surface area and hydrophobicity, while the D-amino acid stereocenter allows systematic comparison of L versus D residue effects on target recognition. Cbz protection supports the synthesis of analog libraries by maintaining orthogonality during coupling steps, followed by deprotection to enable further functionalization or incorporation into larger scaffolds. Downstream derivatives can be generated by converting the carboxyl functionality to activated esters or amides, supporting rapid construction of analog series for medicinal chemistry research.
3. Protected Amino Acid Chemistry
Cbz-4-Methy-D-Phenylalanine serves as a protected amino acid intermediate for derivatization workflows that require a stable N-protected chiral scaffold. The Cbz group provides a predictable protecting-group strategy compatible with common peptide coupling conditions, while the chiral α-carbon stereochemistry is preserved through activation and condensation steps. The aromatic side chain can undergo selective transformations in later stages, including electrophilic aromatic substitution or side-chain functional modifications after the peptide-building sequence is established. Deprotection of the Cbz group can generate a reactive amine for subsequent acylation, conjugation, or formation of additional protected derivatives used in fine chemical synthesis.
4. Chemical Biology Labeling
Cbz-4-Methy-D-Phenylalanine can be incorporated into chemically defined probes for chemical biology experiments that require D-amino acid stability and controlled functional group placement. The protected amine and chiral backbone facilitate stepwise assembly of labeling-ready peptide fragments, where the carboxyl group can be converted into amide-linked handles or further functionalized prior to conjugation. The aromatic side chain contributes to noncovalent association and can support probe localization in binding studies where hydrophobic and π interactions matter. Cbz deprotection enables downstream attachment of reporter groups or affinity tags through amide bond formation, supporting construction of D-peptide conjugates for mechanistic investigations.
5. Pharmaceutical Manufacturing Intermediates
Cbz-4-Methy-D-Phenylalanine is relevant to pharmaceutical manufacturing routes that produce D-amino acid-containing peptide intermediates and peptidomimetic building blocks. The N-Cbz protection strategy supports manufacturing-compatible protection/deprotection cycles, allowing isolation of a stable chiral intermediate during scale-up and enabling controlled release of the amine for subsequent coupling steps. The aromatic side chain with a 4-methyl substituent supports consistent incorporation into defined sequences used to generate impurity-controlled intermediates and characterized synthetic blocks. Downstream processing can include conversion of the carboxyl group into activated forms for amide coupling, supporting scalable assembly of larger peptide structures in industrial fine chemical production.
6. Process Chemistry Intermediate
Cbz-4-Methy-D-Phenylalanine is used in process chemistry as a chiral intermediate for manufacturing peptide fragments and stereochemically defined amino acid derivatives. The robust Cbz-protected amine minimizes undesired side reactions during carboxyl activation and coupling, while the D-stereocenter provides stereochemical fidelity across synthetic steps. The aromatic side chain can influence crystallization behavior and solid-state handling, which can be leveraged during intermediate isolation and purification planning. The resulting deprotected amine and carboxyl functionality can be further transformed into activated intermediates for iterative coupling, supporting efficient production of D-containing peptide building blocks and downstream synthetic targets.
3. Myotropic activity of allatostatins in tenebrionid beetles
4. Store-operated Ca2+ entry sustains the fertilization Ca2+ signal in pig eggs
5. Peptides as Active Ingredients: A Challenge for Cosmeceutical Industry
If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at . We will endeavor to provide highly satisfying products and services.
Creative Peptides is a trusted CDMO partner specializing in high-quality peptide synthesis, conjugation, and manufacturing under strict cGMP compliance. With advanced technology platforms and a team of experienced scientists, we deliver tailored peptide solutions to support drug discovery, clinical development, and cosmetic innovation worldwide.
From custom peptide synthesis to complex peptide-drug conjugates, we provide flexible, end-to-end services designed to accelerate timelines and ensure regulatory excellence. Our commitment to quality, reliability, and innovation has made us a preferred partner across the pharmaceutical, biotechnology, and personal care industries.
Read More