Boc-4-Methoxy-D-Phenylalanine is a protected, non-natural amino acid derivative featuring a phenylalanine backbone bearing a para-methoxy substituent on the aromatic side chain and a D-stereochemical configuration as indicated by the product name. The amino group is protected as a Boc (tert-butoxycarbonyl) carbamate, while the molecule retains a free carboxylic acid functionality, and the methoxy-substituted benzyl side chain provides an aromatic, electron-donating substituent that can influence hydrophobicity and noncovalent interactions in peptide contexts. In peptide chemistry, this Boc-protected amino acid is used as a building block for stepwise incorporation into protected peptide chains, supporting controlled chemoselectivity during amide bond formation and enabling downstream deprotection strategies for the synthesis of modified peptides and structure-activity studies.
CAT No: CP15505
Boc-4-Methoxy-D-Phenylalanine is a D-configured amino acid building block bearing a 4-methoxy-substituted phenyl side chain and an N-terminal Boc (tert-butoxycarbonyl) protecting group. This protected, chiral amino acid is commonly used in peptide and peptidomimetic synthesis where controlled stereochemistry and side-chain electronics are required to probe structure-activity relationships or to build non-natural peptide motifs.
1. Fmoc-Free Peptide Building
Boc-4-Methoxy-D-Phenylalanine is used by peptide synthesis groups that assemble protected amino acid segments using Boc-compatible strategies, including solution-phase workflows and custom segment condensation approaches. The D-configuration helps researchers introduce stereochemical inversion at a defined position, which is frequently leveraged to modulate conformational preferences, proteolytic stability in peptide design studies, and overall scaffold behavior in non-natural peptide analogs. The 4-methoxy-phenyl side chain provides an electronically tuned aromatic group that can support binding-site mimicry in SAR-focused libraries while maintaining the amino acid backbone in a protected form for stepwise assembly.
2. Peptidomimetic SAR Intermediates
Boc-4-Methoxy-D-Phenylalanine serves as a practical intermediate for medicinal chemistry teams developing peptidomimetic series where aromatic substitution patterns are systematically varied. Incorporation of a D-amino acid residue at the target position is often used to generate stereochemically constrained analogs and to differentiate structure-activity trends across analog panels. The methoxy-substituted phenyl side chain supports downstream derivatization planning and analog comparison because it introduces a distinct hydrogen-bond acceptor and steric/electronic profile relative to unsubstituted phenylalanine derivatives, making it valuable for iterative design cycles and library synthesis.
3. Stereodefined Chiral Amino Acid Supply
Boc-4-Methoxy-D-Phenylalanine is frequently selected by custom synthesis providers and research laboratories that require a stereodefined, protected chiral amino acid input for reproducible downstream assembly. The combination of D-stereochemistry with a Boc-protected nitrogen supports consistent incorporation into multi-step synthetic sequences where stereochemical fidelity is critical for interpreting biological or physicochemical structure-property outcomes. The aromatic side chain bearing the 4-methoxy substituent further enables targeted exploration of aromatic ring substitution effects in peptide analogs, including studies aimed at mapping how side-chain electronics influence folding propensity and interaction patterns in chemical biology tool compounds.
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