Cbz-2,5-Dimethy-D-Phenylalanine is a Cbz-protected, non-natural amino acid derivative bearing a substituted phenylalanine backbone with two methyl substituents at the 2- and 5-positions of the aromatic ring and a D-stereochemical configuration as indicated by the name. The molecule contains a free carboxylic acid and an N-terminus carbamate protected by a benzyloxycarbonyl (Cbz) group, while the side chain retains a hydrophobic, aromatic character that can influence steric and electronic properties during peptide assembly. In peptide chemistry and chemical biology, this protected analogue is used as a building block for introducing the 2,5-dimethyl, D-phenylalanine motif into peptides or peptide-related intermediates, supporting structure-activity studies and controlled incorporation of stereochemically defined, sterically modified aromatic residues.
CAT No: CP14009
Cbz-2,5-Dimethy-D-Phenylalanine is a Cbz-protected, chiral phenylalanine derivative bearing a D-configuration at the α-carbon and methyl-substitution at the 2- and 5-positions relative to the amino acid backbone, yielding a sterically defined side chain environment around the aromatic phenyl ring. The benzyloxycarbonyl (Cbz) group masks the amino functionality as a carbamate, while the carboxyl functionality is typically present as a protected or activated form suitable for peptide coupling workflows. The combination of a stereogenic center and ring substitution pattern can influence conformational preferences and steric approach control during amide bond formation, making the compound relevant to stereochemically controlled amino acid derivatization. The aromatic side chain and carbamate protection enable downstream transformations into peptide building blocks, peptidomimetic scaffolds, and chemically addressable intermediates for synthetic methodology development.
1. Peptide Synthesis
Cbz-2,5-Dimethy-D-Phenylalanine is applied in peptide assembly where a Cbz-protected amino acid side chain is required for controlled N-terminal protection and subsequent coupling. The carbamate-protected amine participates in standard peptide coupling strategies after conversion of the carboxyl group to an activated derivative, while the D-configuration at the α-carbon provides stereochemical fidelity for chiral sequence design. The substituted phenyl ring and additional methyl groups can modulate steric effects during coupling and can be used to probe how side-chain bulk impacts peptide conformation and reactivity. The resulting D-amino acid incorporation supports the construction of peptide analogs and protected peptide intermediates that can be further deprotected and elaborated for structure-focused studies in peptide chemistry.
2. Peptidomimetics And SAR
Cbz-2,5-Dimethy-D-Phenylalanine is used in peptidomimetic and SAR-oriented synthesis where aromatic, sterically tuned D-amino acid residues are incorporated to tune binding-site interactions. The protected carbamate allows stepwise synthesis of analog series without premature amine reactivity, while the methyl-substituted phenyl motif can influence hydrophobic contacts, aromatic packing, and local steric constraints. Stereochemical control from the D-α-center supports systematic comparison of stereoisomer effects in structure-activity relationship studies, particularly when designing non-natural peptide scaffolds. Downstream, deprotection and further side-chain functionalization can generate diversified analogs suitable for iterative medicinal chemistry workflows and fragment-to-lead optimization.
3. Protected Amino Acid Chemistry
Cbz-2,5-Dimethy-D-Phenylalanine is suitable for protected amino acid intermediate preparation where stable N-protection and predictable deprotection behavior are required for multi-step synthesis. The Cbz carbamate masks the amino group to prevent undesired side reactions during activation of the carboxyl functionality and during coupling to protected peptide fragments. The chiral center and substituted aromatic ring provide a defined stereochemical and steric profile that can be carried through iterative protection, coupling, and deprotection cycles. The compound can be employed as a chiral building block for generating N-protected D-amino acid derivatives, enabling downstream synthetic routes to chemically consistent peptide building blocks and chiral intermediate libraries.
4. Chemical Biology Probes
Cbz-2,5-Dimethy-D-Phenylalanine is used in chemical biology research to introduce stereochemically defined D-phenylalanine residues into probe scaffolds and labeling-compatible peptide constructs. The Cbz-protected amine supports controlled assembly of peptide-like ligands with minimal interference from free amine chemistry, while the substituted aromatic side chain provides a handle for hydrophobic and π-interaction tuning that can affect molecular recognition. The D-configuration can be leveraged to modulate protease stability and to support selective incorporation into peptide-based probes used for binding studies and pathway interrogation. Deprotected amino acid derivatives derived from this compound can serve as inputs for bioconjugation-ready intermediates, supporting downstream generation of tagged or functionalized molecular probes.
5. Pharmaceutical Intermediate Preparation
Cbz-2,5-Dimethy-D-Phenylalanine is relevant to pharmaceutical intermediate preparation in fine chemical manufacturing where chiral, protected amino acid building blocks are required for controlled synthesis of non-natural peptide components. The carbamate protection strategy enables scalable protection management across multi-step routes, while the stereogenic D-α-center supports consistent stereochemical outcomes in downstream coupling and fragment assembly. The substituted phenyl ring can be carried through process steps to maintain defined steric and electronic features in the final peptide-like intermediate. The compound can therefore function as a process chemistry intermediate for producing protected D-amino acid residues used in larger-scale peptide analog synthesis and medicinal chemistry supply chains.
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