Cbz-2-Methy-L-Phenylalanine is a Cbz-protected, L-configured amino acid derivative in which the side chain corresponds to a phenylalanine framework bearing an additional methyl substituent at the 2-position (α-methyl substitution relative to the parent phenylalanine skeleton). The molecule contains a carbobenzyloxy (Cbz) protecting group on the amino functionality and a free carboxylic acid, while the substituted benzyl side chain provides a hydrophobic aromatic moiety and a sterically modified carbon center that can influence peptide conformations. As a protected amino acid building block, it is used in peptide synthesis workflows to control chemoselectivity during coupling and to introduce the 2-methyl, substituted phenylalanine residue into peptide or peptide-derivative structures for structure-activity and labeling studies.
CAT No: CP15608
Cbz-2-Methy-L-Phenylalanine is a chiral, N-Cbz (benzyloxycarbonyl) protected amino acid derivative featuring an L-configuration at the stereogenic alpha carbon and a 2-methyl substituent that increases steric bulk near the backbone. The molecule contains a protected carbamate at the amino terminus and a free carboxylic acid functionality, enabling controlled peptide coupling after activation while maintaining the stereochemical integrity of the chiral center. The benzyloxycarbonyl group provides stable protection under a range of coupling conditions and can be removed by hydrogenolysis or related deprotection strategies, while the side-chain benzyl aromatic ring supports hydrophobic and π-interaction-driven recognition motifs. As a chiral amino acid intermediate, Cbz-2-Methy-L-Phenylalanine exhibits the reactivity profile typical of protected amino acids, serving as a stereodefined building block for constructing substituted phenylalanine analogs and downstream peptide or peptidomimetic frameworks.
1. Peptide Synthesis
Cbz-2-Methy-L-Phenylalanine supports peptide building-block workflows in solid-phase or solution-phase synthesis, where the free carboxylic acid can be converted to an activated ester or acylating species for amide bond formation. The N-Cbz carbamate protection prevents undesired side reactions during coupling, while the L-stereochemistry at the alpha carbon preserves stereochemical information through sequential peptide assembly. The 2-methyl substitution adjacent to the backbone can influence coupling kinetics and conformational preferences of the resulting peptide segment, making it suitable for constructing sterically modified phenylalanine residues. The resulting peptidic products can be used to probe how α-substitution affects backbone geometry, side-chain packing, and sequence-dependent properties in amino acid chemistry and peptide science.
2. Peptidomimetics And SAR Studies
Cbz-2-Methy-L-Phenylalanine can be employed for peptidomimetic construction and structure-activity relationship studies by enabling incorporation of a sterically biased, substituted phenylalanine motif into bioactive scaffolds. The protected amino group and carboxylic acid functional set allow conversion into amide-linked analogs that retain a defined stereochemical arrangement and aromatic side-chain character. The 2-methyl group can modulate local sterics and hydrogen-bonding patterns, which is relevant when designing analog series to evaluate how subtle backbone modifications alter molecular recognition. Downstream derivatives formed from this building block can serve as SAR-ready intermediates for generating libraries of substituted peptide analogs and conformationally tuned mimetics.
3. Protected Amino Acid Chemistry
Cbz-2-Methy-L-Phenylalanine is well suited to protected amino acid chemistry as an N-Cbz protected, chiral intermediate that can be selectively deprotected and reprotected according to synthetic sequence needs. The Cbz group provides a robust handle for orthogonal protection strategies, allowing the amino terminus to remain masked during carboxyl activation and coupling steps, then removed when unmasking is required for further functionalization or chain elongation. The free carboxylic acid enables transformations such as esterification to form amino acid ester intermediates for process-friendly handling, or activation to generate coupling-ready derivatives. The resulting protected and activated forms support downstream synthetic utility in fine chemical synthesis and stereocontrolled assembly of substituted amino acid derivatives.
4. Chemical Biology Labeling
Cbz-2-Methy-L-Phenylalanine can be applied in chemical biology workflows that require incorporation of substituted phenylalanine residues into probes, affinity tags, or labeled peptide fragments. The aromatic side chain and the stereodefined alpha carbon help maintain physicochemical characteristics associated with phenylalanine-based recognition elements, while the protected amino acid functionality supports stepwise synthesis of conjugatable peptide intermediates. The N-Cbz protection enables controlled generation of terminal amines after deprotection, facilitating subsequent attachment to linkers, dyes, or bioreactive handles through standard amide or carbamate-forming chemistries. The produced labeled or functionalized peptide constructs can then be used for molecular recognition studies, target-binding investigations, and biomolecule modification strategies.
5. Pharmaceutical Intermediate Preparation
Cbz-2-Methy-L-Phenylalanine is suitable for pharmaceutical intermediate preparation where substituted amino acid residues are used to build peptide-like or peptidomimetic components for process chemistry development. The combination of a protected N-terminus and a carboxylic acid provides a predictable platform for manufacturing route design, including conversion to activated acylating agents and controlled coupling into larger intermediates. The stereogenic center and the α-2-methyl substitution support the synthesis of defined stereoisomeric products, which is critical for downstream impurity control and consistent structure-function mapping in medicinal chemistry programs. The intermediate can be further transformed into protected or activated derivatives that integrate into larger synthetic sequences for specialty chemical production and fine chemical manufacturing of amino acid-derived scaffolds.
6. Industrial Fine Chemical Synthesis
Cbz-2-Methy-L-Phenylalanine can be utilized in industrial fine chemical synthesis as a chiral amino acid derivative that fits into scalable, stereocontrolled production of substituted phenylalanine building blocks. The N-Cbz carbamate protection is compatible with common peptide-coupling activation approaches and can be managed through deprotection and refunctionalization steps aligned with manufacturing constraints. The presence of a free carboxylic acid enables downstream derivatization into salts, esters, or activated intermediates that improve handling and facilitate continuous or batch process integration. The resulting derivatives support industrial production of peptide intermediates, peptidomimetic precursors, and process chemistry inputs that rely on stereochemically defined amino acid chemistry.
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