Cbz-4-Methoxy-D-Phenylalanine is a Cbz-protected, D-configured amino acid derivative of phenylalanine bearing a 4-methoxy substituent on the aromatic side chain, placing it in the class of protected aromatic amino acid analogues used for peptide-related synthesis. The molecule contains an N-Cbz carbamate protecting group on the amino functionality and a free carboxylic acid, while the side chain features a para-methoxy phenyl ring that can modulate polarity and aromatic interactions. In synthesis workflows, this protected analogue functions as a stepwise building block for assembling peptide sequences and for preparing modified amino acid residues in chemical biology and structure-activity studies where aromatic substitution patterns are varied.
CAT No: CP15509
Cbz-4-Methoxy-D-Phenylalanine is a D-configured phenylalanine derivative bearing a benzyl oxycarbonyl (Cbz) urethane on the amino group and a 4-methoxy-substituted phenyl side chain that increases aromatic electron density and modulates hydrophobicity. The molecule contains a stereogenic alpha carbon consistent with D-phenylalanine stereochemistry, enabling stereocontrolled peptide coupling and incorporation into chiral sequences. The Cbz carbamate functions as an acid-stable N-protecting group that can be selectively removed under hydrogenolysis conditions, while the aromatic ether (methoxy) provides a handle for downstream functional group transformations such as demethylation or electrophilic aromatic substitution. As a protected amino acid derivative, the compound is well suited for conversion into peptide building blocks and for use as a chiral intermediate in fine chemical synthesis and structure-guided molecular design.
1. Peptide Synthesis
Cbz-4-Methoxy-D-Phenylalanine is applied in peptide coupling chemistry where the Cbz-protected amine and free carboxyl functionality (or carboxyl-activated form) support standard amide bond formation at the alpha position. The D stereocenter and the 4-methoxybenzyl side chain allow incorporation of a stereodefined, aromatic residue into peptide fragments, enabling control of backbone chirality and side-chain sterics. Cbz protection provides compatibility with common peptide coupling conditions and supports orthogonal deprotection strategies during stepwise chain assembly. Downstream, the resulting D-amino-acid-containing peptides can be used to probe sequence effects, generate peptidomimetic scaffolds, and support iterative synthesis of chiral libraries.
2. Peptidomimetics And SAR
Cbz-4-Methoxy-D-Phenylalanine is used in structure-activity relationship studies and peptidomimetic construction where the aromatic side chain and D-configuration influence conformational preferences and receptor-binding geometry. The 4-methoxy substituent can participate in hydrogen-bonding networks as an ether acceptor and can also tune aromatic stacking interactions through electronic effects. Cbz protection enables reliable incorporation into analog series while maintaining a protected handle for later deprotection and functionalization. The compound can therefore serve as a chiral residue precursor for generating D-amino-acid-substituted analogs used in SAR workflows and molecular design campaigns.
3. Side-Chain Functionalization
Cbz-4-Methoxy-D-Phenylalanine is suitable for side-chain functionalization routes that leverage the methoxy-bearing aromatic ring as a synthetic intermediate. The aryl ether can undergo demethylation to reveal a phenolic handle, enabling subsequent derivatization such as esterification, ether formation, or coupling to electrophiles for targeted conjugation chemistries. The Cbz carbamate protects the amino functionality during side-chain transformations, reducing undesired reactions and supporting chemoselective modifications. Generated functionalized derivatives can then be carried forward as chiral amino acid building blocks for labeled probes, affinity reagents, and intermediate preparation in applied synthetic organic chemistry.
4. Chiral Building Block Synthesis
Cbz-4-Methoxy-D-Phenylalanine is applied as a chiral amino acid intermediate in asymmetric and stereocontrolled synthesis where the D-phenylalanine stereocenter provides defined stereochemical information to downstream molecules. The protected carbamate (Cbz) stabilizes the amino group during intermediate conversions, supporting manufacturing-relevant sequences that require protection of nitrogen while other functional groups are manipulated. The aromatic side chain with a methoxy substituent provides a stable scaffold for conversion into additional chiral fragments, including aromatic-containing heteroaromatic precursors or substituted aromatic motifs. The compound can be employed to prepare stereodefined intermediates for fine chemical synthesis and for constructing chiral libraries used in chemical discovery and materials-oriented research.
5. Bioconjugation Chemistry
Cbz-4-Methoxy-D-Phenylalanine is relevant to bioconjugation workflows where D-amino-acid-containing peptide segments improve stability against proteolysis and provide defined stereochemistry for controlled coupling. The Cbz-protected amino group supports stepwise assembly into peptide conjugates, while later Cbz removal enables access to a free amine for conjugation or further derivatization. The 4-methoxy aromatic side chain can be retained to modulate hydrophobicity and interaction profiles of the conjugate, or transformed to a phenolic group to enable additional coupling chemistries. Resulting D-amino-acid-bearing conjugation intermediates can be used to generate biomolecule-modified probes, affinity reagents, and chemically defined peptide-based materials.
6. Pharmaceutical Intermediate Preparation
Cbz-4-Methoxy-D-Phenylalanine is used in pharmaceutical intermediate preparation and process chemistry contexts where protected D-amino acid building blocks are required for manufacturing of chiral peptide-like structures. The Cbz carbamate offers a practical nitrogen protection strategy that can be carried through coupling and intermediate transformations, supporting route design that separates protection, coupling, and final deprotection steps. The presence of an aromatic methoxy substituent provides a consistent functional motif for downstream derivatization into substituted aromatic pharmacophore elements or for generating analog series. The compound therefore functions as a stereodefined, protected amino acid intermediate that can be incorporated into larger synthetic sequences for fine chemical production and applied medicinal chemistry programs.
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