Cbz-2,6-Dimethy-D-Phenylalanine is a protected, non-proteinogenic amino acid derivative featuring a benzyl-protected carboxyl group via a Cbz (benzyloxycarbonyl) protecting group and a substituted phenylalanine backbone bearing 2,6-dimethyl substitution on the aromatic ring, with the stereochemical form indicated as D. The molecule contains a free amino functional group and a carboxyl functionality masked as the Cbz carbamate, while the 2,6-dimethylphenyl side chain provides a sterically hindered, hydrophobic aromatic surface that can influence peptide coupling and conformational preferences. In synthetic peptide chemistry and chemical biology workflows, it is employed as a protected amino acid building block to introduce the sterically encumbered, dimethyl-substituted phenylalanine residue into peptide or peptidomimetic structures and to support structure-activity studies or labeling strategies where aromatic sterics and hydrophobicity are varied.
CAT No: CP14109
Cbz-2,6-Dimethy-D-Phenylalanine is a chiral, N-Cbz-protected phenylalanine derivative bearing a D-configuration at the α-carbon and two methyl substituents at the 2- and 6-positions of the aromatic ring. The molecule contains a carbamate-protected amine (benzyloxycarbonyl, Cbz) and a free carboxylic acid, enabling controlled peptide coupling while preserving stereochemical integrity during synthesis. The ortho-disubstituted phenyl side chain increases steric bulk and modulates aromatic reactivity, which can influence amide formation rates and downstream derivatization of the side-chain environment. The combination of a stable protecting group and a functionalized chiral side chain makes the compound a practical intermediate for stereodefined peptide building blocks and chiral amino acid modification workflows.
1. Peptide Synthesis
Cbz-2,6-Dimethy-D-Phenylalanine supports peptide coupling chemistry in solid-phase or solution-phase synthesis where a Cbz-protected amino acid is required. The Cbz carbamate protects the amino functionality during activation of the carboxylic acid, while the D-configuration at the α-carbon enables stereochemically defined incorporation into peptide sequences. The 2,6-dimethyl-substituted phenyl side chain can be used to tune steric effects in peptide backbones, affecting conformational preferences and protecting-group compatibility during iterative chain assembly. The resulting D-amino acid-containing peptides can serve as standards or scaffold elements for studying stereochemical effects in peptide science and peptidomimetic design.
2. Peptidomimetics And SAR Studies
Cbz-2,6-Dimethy-D-Phenylalanine is suitable for structure-activity relationship studies where aromatic side-chain sterics and stereochemistry are systematically varied. The ortho-disubstituted phenyl ring provides a defined, bulky hydrophobic motif that can modulate binding pocket occupancy and local conformational constraints when incorporated into peptidomimetics. The Cbz-protected amine and free carboxylic acid enable conversion into amide-linked analogs that can be compared across series while maintaining consistent protection/deprotection logic. The D-amino acid stereocenter further supports SAR workflows that probe how inversion at the α-carbon alters molecular recognition and peptide-like behavior.
3. Chiral Building Block Development
Cbz-2,6-Dimethy-D-Phenylalanine functions as a chiral amino acid intermediate for stereoselective synthesis routes that require a D-configured phenylalanine analog. The preserved stereocenter and the robust Cbz group allow orthogonal handling of the nitrogen and carboxyl functionalities, supporting sequential transformations such as activation for coupling followed by controlled deprotection when needed. The 2,6-dimethyl substitution pattern can be leveraged to create sterically shielded aromatic environments that reduce undesired side reactions during intermediate fabrication. Downstream, the compound can be employed to generate libraries of D-amino acid derivatives for asymmetric synthesis planning, fragment elaboration, and stereodefined molecular scaffold construction.
4. Side-Chain Functionalization
Cbz-2,6-Dimethy-D-Phenylalanine can be applied to side-chain functionalization strategies that exploit the aromatic ring as a derivatization handle while maintaining the amino acid framework. The ortho-dimethyl substitution pattern can influence electrophilic aromatic substitution, metalation behavior, and steric accessibility, enabling selective chemistry on the aromatic moiety under conditions compatible with peptide-grade intermediates. The Cbz-protected amine and carboxylic acid allow the compound to be carried through derivatization steps as a protected amino acid, supporting later conversion into amides or activated intermediates for conjugation. The resulting functionalized D-phenylalanine derivatives can serve as inputs for chemical biology probes, binding-site mapping reagents, and peptidomimetic analog generation.
5. Pharmaceutical Intermediate Preparation
Cbz-2,6-Dimethy-D-Phenylalanine is relevant to pharmaceutical intermediate preparation where D-amino acid building blocks are incorporated into peptide-like small molecules or constrained peptidomimetics. The carbamate-protected nitrogen and free acid align with common manufacturing logic for protected amino acid synthesis, activation, and subsequent coupling to form amide linkages under controlled stereochemical constraints. The bulky 2,6-dimethylphenyl side chain can be used to modulate physicochemical properties such as hydrophobicity and steric shielding in downstream intermediates, which can be important for processable, stable analog design. The compound can therefore serve as a defined chiral precursor for downstream synthesis of protected peptide fragments and D-amino acid-containing intermediates used in fine chemical production.
6. Analytical Research Standards
Cbz-2,6-Dimethy-D-Phenylalanine can be used in analytical research to support method development and stereochemical verification for amino acid and peptide workflows. The presence of a Cbz-protected amine and a D-configured α-center provides a distinct, well-defined chemical signature that can aid LC-MS or chromatographic separation of stereoisomeric amino acid derivatives. The 2,6-dimethyl-substituted phenyl side chain contributes to predictable retention behavior and fragmentation patterns, supporting identification of D-phenylalanine-containing products and monitoring of coupling or deprotection steps. The compound can be employed as a reference material for characterizing peptide building block incorporation and for supporting quality control of stereodefined amino acid derivatives in research and industrial settings.
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