Cbz-2,6-Dimethy-L-Phenylalanine is a Cbz-protected, substituted phenylalanine derivative in which the phenyl side chain bears two methyl substituents at the 2- and 6-positions, retaining an L-configuration at the alpha carbon as indicated by the name. The molecule contains a free carboxyl functional group or carboxyl equivalent appropriate for amino acid chemistry alongside a benzyl carbamate (Cbz) protecting group on the amino functionality, while the bulky, ortho-disubstituted aromatic side chain provides a sterically hindered, hydrophobic aromatic environment. In peptide synthesis and related peptide chemistry workflows, this protected amino acid is used as a building block to introduce the sterically modified aromatic residue into peptide sequences and to support stepwise coupling by maintaining the amino group in a protected, chemoselective form.
CAT No: CP14108
Cbz-2,6-Dimethy-L-Phenylalanine is a Cbz-protected, L-configured phenylalanine derivative in which the side chain bears two methyl substituents at the 2,6-positions of the aromatic ring, creating a sterically hindered, substituted benzyl side chain. The molecule contains a carbobenzyloxy (Cbz) group on the amino functionality and a carboxylic acid handle (or an acid-equivalent form depending on supplier specification), enabling controlled peptide coupling chemistry while maintaining stereochemical integrity at the α-carbon. The aromatic ring with ortho-disubstitution modulates conformational preferences and can influence reactivity during electrophilic aromatic substitutions and side-chain functionalization steps. The combination of an N-protecting group and a chiral amino acid framework makes the compound a practical chiral building block for protected amino acid synthesis, peptide assembly, and downstream derivatization into sterically defined aromatic analogs.
1. Peptide Synthesis
Cbz-2,6-Dimethy-L-Phenylalanine supports peptide building-block preparation for solid-phase or solution-phase peptide synthesis where an N-protected amino acid is required to control chemoselectivity. The Cbz-protected amine participates in standard peptide coupling after activation of the carboxyl group, while the L-stereocenter preserves the intended backbone stereochemistry for amide bond formation. The 2,6-dimethyl substituted phenyl side chain can be incorporated into peptides to tune steric bulk, aromatic packing, and local conformation, which can be relevant for generating peptide libraries and sequence variants. The resulting protected residue can be further processed through Cbz removal under hydrogenolysis-compatible conditions, enabling iterative chain elongation and producing defined aromatic peptide analogs.
2. Peptidomimetics And SAR Studies
Cbz-2,6-Dimethy-L-Phenylalanine serves as a chiral starting point for peptidomimetic construction and structure-activity relationship studies that require sterically constrained aromatic side chains. The ortho-disubstituted aromatic ring can act as a conformational and steric modulator, affecting intramolecular interactions and side-chain orientation in peptide-like scaffolds. The Cbz-protected amino group and carboxyl functionality allow conversion into amide-linked analogs, including non-natural peptide fragments and constrained backbone mimics. Downstream derivatization of the aromatic ring or side-chain environment can be applied to SAR workflows that compare steric and electronic effects across closely related amino acid substitutions.
3. Chemical Biology Labeling
Cbz-2,6-Dimethy-L-Phenylalanine can be utilized in chemical biology workflows that require incorporation of a defined, sterically hindered aromatic residue into probes or affinity ligands. The protected amino acid framework enables controlled incorporation into peptide tags, receptor-binding peptides, or enzyme-interacting sequences before selective deprotection and conjugation steps. The 2,6-dimethyl substituted phenyl side chain provides a hydrophobic aromatic motif that can influence binding pocket accommodation and can help reduce undesired side reactions from more reactive aromatic patterns. The Cbz group supports sequential functionalization strategies, allowing the residue to be positioned within larger biomolecular constructs prior to downstream coupling to labeling handles.
4. Protected Amino Acid Intermediates
Cbz-2,6-Dimethy-L-Phenylalanine functions as a protected amino acid intermediate for manufacturing-grade fine chemical synthesis routes that prioritize stable storage and predictable coupling behavior. The Cbz protecting group on the α-amino functionality supports chemoselective peptide coupling chemistry and can be removed when needed to expose the free amine for subsequent transformations. The L-configuration and substituted aromatic side chain provide a defined stereochemical and structural motif for producing sequence-specific intermediates used in peptide building block supply chains. The compound's protected/functional group pattern can be integrated into downstream synthesis of aromatic amino acid derivatives, including analogs bearing additional side-chain modifications for industrial intermediate preparation and process development.
5. Process Chemistry For Aromatic Analogues
Cbz-2,6-Dimethy-L-Phenylalanine may be applied in process chemistry for producing sterically defined aromatic amino acid analogs used in specialty chemical manufacturing. The molecule's N-protection strategy via Cbz and the presence of a carboxyl functionality support scalable coupling and purification workflows that rely on orthogonal reactivity between protected and deprotected states. The 2,6-dimethyl substitution pattern can improve handling by reducing certain aromatic side reactions while still allowing controlled derivatization when required for target intermediates. The resulting chiral aromatic building block can be routed into larger peptide or peptidomimetic manufacturing sequences, supporting consistent stereochemical outcomes and reproducible intermediate quality for downstream synthesis.
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