Cbz-3,4-Dimethy-D-Phenylalanine is a Cbz-protected, non-proteinogenic amino acid derivative bearing a substituted phenylalanine backbone with a 3,4-dimethyl substitution on the aromatic side chain and a D stereochemical configuration as indicated by the name. The molecule contains an N-terminal benzyloxycarbonyl (Cbz) protecting group that masks the amino functionality and a free carboxylic acid, while the aromatic side chain provides hydrophobic character and a sterically modified ring suitable for structure-activity and conformational studies. In peptide chemistry, it functions as a protected amino acid building block for stepwise coupling in peptide synthesis workflows, including the preparation of analog-containing peptides and related chemical biology probes where the modified aromatic substitution pattern is required.
CAT No: CP14209
Cbz-3,4-Dimethy-D-Phenylalanine is a D-configuration phenylalanine derivative bearing a benzyl carbamate (Cbz) on the alpha-amino group and a substituted aromatic side chain with 3,4-dimethyl substitution. The chiral center at the amino acid alpha position and the D-stereochemistry make it a defined stereochemical building block for stereocontrolled peptide coupling and for preparing chiral amino acid intermediates. The Cbz-protected amine provides a stable handle during acid/base manipulation and peptide bond formation, while the aromatic ring with methyl substituents tunes hydrophobicity and steric environment for molecular recognition studies. The compound's protected amino acid framework and side-chain functionality support downstream transformations such as deprotection to reveal a reactive amino group and further derivatization into peptide analogs, chiral ligands, or synthetic intermediates for fine chemical production.
1. Protected Amino Acid Synthesis
Cbz-3,4-Dimethy-D-Phenylalanine is applied in protected amino acid synthesis workflows where a carbamate-protected D-amino acid is required for controlled peptide coupling chemistry. The Cbz group on the alpha-amine is compatible with common coupling conditions and can be removed selectively to regenerate the free amine for subsequent functionalization steps. The 3,4-dimethyl substituted phenyl side chain provides a defined hydrophobic/aromatic motif that can be retained through protection, coupling, and deprotection sequences. The resulting intermediate supports stepwise construction of peptide building blocks and chiral amino acid derivatives used in synthetic organic chemistry and biochemical research intermediate preparation.
2. Peptide Synthesis
Cbz-3,4-Dimethy-D-Phenylalanine is suitable for peptide synthesis and peptide fragment assembly where D-amino acid incorporation is used to modulate backbone stereochemistry and conformational preferences. The protected alpha-amino functionality enables formation of amide bonds through standard peptide coupling strategies while maintaining the D-configuration at the stereogenic center. The substituted phenyl side chain with 3,4-dimethyl substitution can influence steric bulk and aromatic packing in the growing peptide, supporting the construction of D-enriched analogs for structure-activity relationship studies. The Cbz-protected amino acid framework also supports iterative synthesis of protected peptide segments and downstream deprotection to yield coupling-ready residues for longer chain assembly.
3. Peptidomimetics And SAR Studies
Cbz-3,4-Dimethy-D-Phenylalanine is utilized in peptidomimetic and SAR studies where incorporation of a D-phenylalanine analog helps probe stereochemical effects on target binding motifs. The D-stereochemistry and Cbz-protected amine allow incorporation into peptide-like scaffolds while preserving a defined stereochemical identity through synthesis and purification. The 3,4-dimethyl substituted aromatic ring can serve as a tunable hydrophobic/aromatic pharmacophore, enabling systematic exploration of side-chain steric and electronic influences across analog series. The protected amino acid derivative can be converted into multiple downstream peptide analogs and fragment-based constructs that support iterative medicinal chemistry and SAR-driven molecular design.
4. Chemical Biology Labeling
Cbz-3,4-Dimethy-D-Phenylalanine can be applied in chemical biology labeling strategies that require chiral amino acid residues for incorporation into probes, affinity ligands, or constrained peptide tags. The Cbz-protected alpha-amine supports controlled peptide conjugation chemistry, enabling attachment to carrier peptides or scaffold proteins after selective deprotection. The substituted phenyl side chain provides an aromatic element that can participate in hydrophobic contacts and can be retained as a stable motif during conjugate assembly and downstream processing. The resulting labeled constructs can serve as research reagents for studying biomolecular interactions, mapping binding determinants, and generating defined stereochemical variants for mechanistic biochemical investigation.
5. Process Chemistry Intermediate
Cbz-3,4-Dimethy-D-Phenylalanine is relevant to process chemistry intermediate preparation where a protected D-amino acid is needed as a manufacturable input for fine chemical synthesis. The carbamate protection pattern supports handling under conditions that would otherwise compromise unprotected amines, enabling robust intermediate management during multi-step synthesis. The stereochemical definition at the alpha carbon supports consistent downstream composition for peptide building block preparation and for producing stereochemically defined analog libraries. The compound's protected amino acid structure also aligns with industrially scalable synthetic planning, including protection/deprotection sequencing and conversion into coupling-ready derivatives for downstream manufacturing of peptide-related intermediates.
2. Store-operated Ca2+ entry sustains the fertilization Ca2+ signal in pig eggs
5. Emerging applications of nanotechnology for diagnosis and therapy of disease: a review
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