Cbz-2-Methoxy-D-Phenylalanine is a Cbz-protected, non-natural amino acid derivative featuring a phenylalanine backbone bearing a 2-methoxy substituent on the alpha-carbon region and a D stereochemical configuration as indicated by the name. The molecule contains a carboxyl functionality masked under a carbamate-protecting group (Cbz) on the amino acid nitrogen, while the side chain retains the benzyl-like aromatic ring and the alpha-substituted 2-methoxy group provides an additional ether functionality for controlled polarity and hydrogen-bonding behavior. As a protected amino acid building block, it is employed in peptide synthesis workflows and structure-activity or chemical biology studies where incorporation of an alpha-ether-substituted, D-configured phenylalanine analogue is used to probe sequence-dependent properties or to generate defined peptide and conjugate intermediates.
CAT No: CP15309
Cbz-2-Methoxy-D-Phenylalanine is a Cbz-protected D-phenylalanine derivative featuring a side-chain aromatic ring and an ether-substituted alpha-carbon substituent (2-methoxy) that defines its stereochemical identity. The molecule contains a benzyloxycarbonyl (Cbz) carbamate on the amino function, a methyl ether group that modulates polarity and hydrogen-bonding capacity, and a free carboxyl functionality or carboxyl derivative depending on the supplied form. The D-configuration at the stereogenic center and the aromatic side chain make it a chiral amino acid building block for stereocontrolled peptide coupling and for constructing peptidomimetic scaffolds with defined spatial relationships. The Cbz protecting group is chemically compatible with common peptide synthesis workflows and can be removed under standard hydrogenolysis conditions to reveal a reactive amine for downstream derivatization.
1. Peptide Synthesis
Cbz-2-Methoxy-D-Phenylalanine is used in peptide building block preparation where a protected amino group and a defined D-amino acid stereocenter support reliable peptide coupling chemistry. The Cbz carbamate protects the alpha-amine during activation of the carboxyl functionality, while the 2-methoxy substituent and phenyl side chain influence conformational preferences and side-chain electronics in the growing chain. The aromatic residue can participate in hydrophobic and π-interaction patterns that are relevant for peptide folding studies and for constructing D-amino acid-rich sequences that resist proteolysis. Deprotection of the Cbz group enables sequential N-terminal functionalization, supporting iterative synthesis of protected and deprotected peptide intermediates for research-grade peptide libraries and process-relevant oligopeptide manufacture.
2. Chiral Amino Acid Intermediate
Cbz-2-Methoxy-D-Phenylalanine serves as a chiral amino acid intermediate for stereoselective synthesis of enantiomerically defined derivatives and unnatural amino acid analogs. The D-configuration at the alpha-carbon provides a fixed stereochemical handle for downstream transformations that retain stereochemical integrity through protected-amino handling and controlled coupling steps. The 2-methoxy ether can be leveraged as a stability-tuned functional group that may be retained, substituted, or converted after incorporation into larger molecules, enabling structure-guided derivatization strategies. The Cbz-protected amine also supports orthogonal protection schemes, allowing selective deprotection and re-protection sequences when designing multi-functional chiral intermediates for fine chemical synthesis.
3. Peptidomimetics And SAR Studies
Cbz-2-Methoxy-D-Phenylalanine is applied in peptidomimetic construction and structure-activity relationship studies where side-chain substitution and stereochemistry are used to tune molecular recognition. The phenylalanine aromatic side chain provides a hydrophobic and π-interaction element, while the 2-methoxy substituent introduces an ether oxygen that can affect local polarity and hydrogen-bond acceptor availability in the analog. Incorporation of the D-amino acid motif can be used to probe stereochemical contributions to binding and conformational stability without relying on natural L-amino acid geometry. The Cbz-protected amine supports controlled assembly of analog series, and subsequent deprotection and functional group interconversions can generate diversified derivatives for SAR mapping and fragment-to-lead optimization workflows.
4. Chemical Biology Conjugation
Cbz-2-Methoxy-D-Phenylalanine can be employed in chemical biology workflows that require protected amino acid handles for conjugation chemistry and biomolecule modification. The Cbz carbamate enables temporary masking of the amine during synthesis of linkers or peptide-based probes, while the phenyl side chain and methoxy group can be used to modulate solubility and reactivity of the final conjugate. Deprotection of the Cbz group yields a primary amine suitable for coupling to activated esters, isothiocyanates, aldehyde-derived linkers, or other electrophiles used to attach the amino acid residue to proteins, polymers, or affinity reagents. The stereodefined D-amino acid character supports probe stability and can help maintain consistent spatial orientation of the conjugation point across probe variants used in labeling and molecular recognition studies.
5. Pharmaceutical Intermediate Preparation
Cbz-2-Methoxy-D-Phenylalanine is relevant to pharmaceutical intermediate preparation and process chemistry for manufacturing peptide-like building blocks and chiral fragments used in drug discovery supply chains. The protected carbamate functionality supports safe handling during scale-up steps where amine reactivity must be controlled, and the defined D-stereocenter reduces variability in downstream coupling and analog synthesis. The aromatic side chain and methoxy ether can be carried through intermediate stages to preserve structural features required for later elaboration into larger active-molecule candidates or metabolically tuned analogs. The compound's compatibility with standard amino acid protection/deprotection logic makes it suitable for building block strategies that streamline the preparation of protected amino acid derivatives and their incorporation into multi-step synthetic routes.
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