Cbz-2,3-Dimethy-D-Phenylalanine is a Cbz-protected, non-natural amino acid derivative featuring a phenylalanine backbone bearing two methyl substituents at the 2- and 3-positions of the side chain and a D-configuration at the alpha carbon as indicated by the name. The molecule contains a carboxyl group masked as a protected amino acid functionality under the Cbz (benzyloxycarbonyl) group on the amino terminus, while the side chain retains a substituted aromatic ring and the backbone presents the characteristic amino acid framework for peptide coupling chemistry. In peptide synthesis and chemical biology workflows, this protected analogue functions as a stepwise building block that provides chemoselective control of the amino functionality while the sterically modified, methyl-substituted phenyl side chain can be incorporated into peptides or used in structure-activity and labeling studies to probe effects of altered side-chain topology.
CAT No: CP13809
Cbz-2,3-Dimethy-D-Phenylalanine is a Cbz-protected D-phenylalanine derivative bearing two methyl substituents at the 2- and 3-positions of the amino acid backbone, creating a sterically congested, chiral, non-natural residue. The molecule contains a benzyloxycarbonyl (Cbz) carbamate on the amino group, a carboxylic acid functionality suitable for activation and coupling, and a pendant phenyl ring that supports hydrophobic and aromatic interactions in peptide contexts. The D stereochemistry at the α-carbon and the additional methyl substitution pattern influence conformational preferences and side-chain/ backbone sterics, which can affect peptide folding and receptor/target recognition in structure-based design. The Cbz protecting group and the hindered backbone can be used to tune reactivity during protected amino acid synthesis, peptide coupling, and subsequent deprotection to downstream intermediates.
1. Peptide Synthesis
Cbz-2,3-Dimethy-D-Phenylalanine is applied in peptide building workflows where a protected, chiral amino acid residue is required for controlled amide bond formation. The Cbz carbamate protects the amino functionality during coupling chemistry, while the carboxylic acid can be converted to activated esters or mixed anhydrides to enable peptide coupling at the C-terminus of the growing chain. The 2,3-dimethyl substitution pattern on the backbone increases steric bulk near the amide linkage, which can be leveraged to modulate local conformation and proteolytic stability of peptide analogs. D-configuration incorporation supports stereochemically defined unnatural peptide sequences for research-grade peptide construction and subsequent deprotection to reveal the free amine for further assembly.
2. Peptidomimetics And SAR
Cbz-2,3-Dimethy-D-Phenylalanine is used in peptidomimetic design and structure-activity relationship studies where backbone methylation and D stereochemistry are used to tune binding conformations. The phenylalanine-derived aromatic side chain and the additional 2,3-dimethyl groups can alter steric footprint and hydrophobic contact patterns relative to canonical phenylalanine residues. The Cbz-protected amino group allows stepwise incorporation into peptide scaffolds without premature amine reactivity, supporting iterative synthesis of analog series with controlled stereochemical identity. The resulting D-methylated residue can serve as a defined fragment in SAR mapping, enabling downstream generation of analogs for biochemical screening workflows and target-binding studies.
3. Chiral Synthesis Intermediate
Cbz-2,3-Dimethy-D-Phenylalanine functions as a chiral amino acid intermediate for stereoselective synthetic organic chemistry routes that require a D-configured, sterically hindered building block. The molecule's single, well-defined stereocenter at the α-position and the fixed methyl substitution pattern provide a rigid stereochemical handle for constructing higher-order chiral frameworks through amide formation and subsequent functional group transformations. The Cbz group provides orthogonal protection that can be removed under hydrogenolysis-compatible conditions, enabling sequential deprotection strategies when multiple protected functionalities are present in a synthetic sequence. The carboxylic acid and protected amine combination supports conversion into peptide building block derivatives, activated coupling species, or further protected amino acid intermediates used in fine chemical synthesis.
4. Side-Chain Functionalization
Cbz-2,3-Dimethy-D-Phenylalanine is suitable for side-chain and backbone functionalization strategies that generate non-natural amino acid derivatives for chemical biology tools. The phenyl ring can be retained as an aromatic anchor while the sterically modified backbone can influence subsequent derivatization outcomes, such as selective transformations after incorporation into larger molecules. The Cbz-protected amine enables controlled chemistry during intermediate preparation, including formation of peptide-linked constructs that later undergo deprotection to expose reactive amine sites for conjugation or further coupling. The resulting functionalized amino acid derivatives can be used to generate labeled or modified peptide conjugates, supporting downstream molecular recognition studies and reagent synthesis in applied amino acid chemistry.
5. Pharmaceutical Intermediate Preparation
Cbz-2,3-Dimethy-D-Phenylalanine is relevant to pharmaceutical intermediate preparation where protected amino acid residues are incorporated into peptidic or peptidomimetic intermediates during process chemistry. The Cbz carbamate protection supports compatibility with common peptide coupling conditions by minimizing side reactions from the amino functionality, while the carboxylic acid enables conversion to coupling-ready intermediates for manufacturing-scale synthetic sequences. The D stereochemistry and 2,3-dimethyl backbone substitution can be used to establish defined stereochemical content in final active or intermediate structures that require non-natural residue incorporation. The compound's protected amino acid architecture therefore supports downstream synthesis of stereochemically defined peptide fragments and intermediate streams used in specialty chemical production and chemical manufacturing workflows.
6. Analytical Research Standard
Cbz-2,3-Dimethy-D-Phenylalanine can be employed as an analytical reference material component for method development and characterization of peptide synthesis products containing D-methylated phenylalanine residues. The distinct molecular structure, including the Cbz-protected carbamate and the 2,3-dimethyl substitution pattern, provides chromatographic and mass spectrometric signatures that help confirm residue identity and stereochemical incorporation in complex mixtures. The carboxylic acid and protected amine functional groups enable derivatization into coupling analogs or internal standards that mirror the chemistry of peptide building block preparation. The compound supports analytical verification workflows such as LC-MS-based monitoring of protected amino acid incorporation, deprotection progress, and impurity profiling for peptide science and applied amino acid chemistry.
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