Fmoc-2-Methoxy-D-Phenylalanine is a protected, non-natural amino acid derivative in which the phenylalanine scaffold is modified at the 2-position by a methoxy substituent and the amino acid is presented in the D stereochemical form as indicated by the product name. The molecule contains a free carboxyl group and an Fmoc-protected amino group, with the side chain retaining a benzyl-like aromatic functionality and the 2-methoxy substituent altering the alpha-carbon substitution pattern and polarity. As an Fmoc-protected building block, it is used in peptide synthesis workflows to introduce this substituted D-phenylalanine residue into peptide sequences and to support structure-activity studies, chemical labeling strategies, and conformational or physicochemical property investigations of peptide analogues.
CAT No: CP15307
Fmoc-2-Methoxy-D-Phenylalanine is an Fmoc-protected, D-configured phenylalanine derivative in which the side chain bears a 2-methoxy substituent, creating a stereochemically defined amino acid building block for peptide and peptidomimetic assembly. The molecule contains an N-(9H-fluoren-9-ylmethoxycarbonyl) protecting group on the amino functionality, a free carboxyl group suitable for coupling chemistry, and a chiral center at the alpha position that enables incorporation of D-amino acid stereochemistry into synthetic sequences. The aromatic side chain with a methoxy substituent introduces an additional electron-donating functional group that can influence conformational preferences, aromatic interactions, and downstream derivatization options. The protected amine and carboxylic acid combination supports standard peptide coupling workflows and subsequent Fmoc deprotection strategies, while the methoxy-bearing aryl motif can participate in controlled functional group transformations for SAR-oriented scaffold diversification.
1. Peptide Synthesis
Fmoc-2-Methoxy-D-Phenylalanine is used in solid-phase peptide synthesis and related peptide building workflows to introduce a D-amino acid residue with a methoxy-substituted phenyl side chain. The Fmoc-protected nitrogen enables orthogonal handling during chain elongation, while the free carboxyl group participates in amide bond formation under peptide coupling conditions. The D-configuration at the alpha stereocenter supports access to stereochemically defined peptide analogs that can modulate backbone orientation and protease resistance profiles in structure-function studies. The methoxy substituent on the aromatic ring can be retained through peptide assembly or used as a handle for later functionalization, supporting downstream analog generation from a single chiral intermediate.
2. Peptidomimetics And SAR
Fmoc-2-Methoxy-D-Phenylalanine is applied in peptidomimetic construction and structure-activity relationship (SAR) studies where stereodefined aromatic side-chain electronics are used to tune molecular recognition. The combination of an Fmoc-protected amino acid backbone and a D-amino acid stereocenter supports systematic variation of peptide-like scaffolds while maintaining consistent coupling compatibility. The 2-methoxy phenyl group can influence hydrophobic surface properties and aromatic interaction patterns, enabling rational design of analog series that probe binding-site preferences. The resulting peptide analogs and constrained derivatives can serve as research-grade SAR intermediates for medicinal chemistry exploration and biochemical assay development.
3. Protected Amino Acid Chemistry
Fmoc-2-Methoxy-D-Phenylalanine is suitable for protected amino acid chemistry workflows that require an Fmoc-compatible, chiral intermediate for N-protection strategies and controlled deprotection sequencing. The Fmoc group provides a stable N-protected form during synthetic manipulations, while the carboxylic acid functionality supports conversion to activated coupling derivatives or direct incorporation into peptide sequences. The D-configuration enables stereochemically controlled synthesis of enantiopure sequences and supports the preparation of D-amino acid-rich libraries for stereochemical mapping. The methoxy-substituted aromatic side chain can remain intact during Fmoc deprotection and coupling, supporting predictable downstream transformations when additional functional group modification is required.
4. Side-Chain Functionalization
Fmoc-2-Methoxy-D-Phenylalanine is employed as a chiral side-chain functionalization precursor for generating diversified aromatic derivatives while preserving the D-amino acid framework. The methoxy substituent on the phenyl ring provides a chemically meaningful handle for transformations such as demethylation to phenol derivatives or further aromatic functional group elaboration, depending on the synthetic plan. The presence of an Fmoc-protected amine and a carboxyl group allows sequential strategy design where peptide coupling compatibility is maintained until side-chain modification steps are executed. The resulting functionalized amino acid derivatives can be used to build analogs with altered hydrogen-bonding capacity and aromatic reactivity, supporting fine-tuning in chemical biology research and synthetic organic chemistry programs.
5. Pharmaceutical Manufacturing Intermediates
Fmoc-2-Methoxy-D-Phenylalanine is relevant to pharmaceutical manufacturing and fine chemical production contexts that require reproducible chiral amino acid inputs for peptide intermediate synthesis. The Fmoc-protected format supports scalable peptide building block preparation and controlled deprotection/coupling sequences compatible with process-oriented solid-phase or solution-phase manufacturing strategies. The defined D-stereochemistry and methoxy-substituted aromatic side chain contribute to consistent impurity profiles and predictable downstream derivative formation when incorporated into larger peptide intermediates. The compound can serve as a process chemistry intermediate for producing stereochemically specified peptide components used in manufacturing of peptide-based research materials and process development batches.
6. Analytical Research Standards
Fmoc-2-Methoxy-D-Phenylalanine is utilized in analytical research for method development and reference standard preparation involving Fmoc-amino acid derivatives and D-amino acid-containing peptides. The stable Fmoc protecting group and the characteristic methoxy-substituted aromatic side chain provide distinguishable chromatographic and spectrometric signatures for monitoring coupling efficiency, deprotection behavior, and identity confirmation in peptide synthesis workflows. The defined stereochemistry at the alpha carbon supports stereospecific analytical comparisons for chiral separation studies and for verifying incorporation of D-amino acid residues in peptide analogs. The compound can be applied as a structural benchmark in quality control-oriented analytical method validation and in characterization of peptide intermediates and side-chain-modified derivatives.
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