N-Fmoc-N-methyl-3-methoxy-L-phenylalanine is an aromatic amino acid analog featuring methoxy substitution and N-methylation. The combined modifications affect stacking, polarity, and backbone rigidity. Researchers employ it in designed hydrophobic cores and constrained peptide motifs. Its protections support stepwise synthetic incorporation.
CAT No: R2130
CAS No:2642331-21-1
Synonyms/Alias:N-FMOC-N-METHYL-3-METHOXY-L-PHENYLALANINE;2642331-21-1;(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl](methyl)amino}-3-(3-methoxyphenyl)propanoic acid;N-Fmoc-N-Me-L-Phe(3-OMe)-OH;F95705;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-(3-methoxyphenyl)propanoic acid;
N-Fmoc-N-methyl-3-methoxy-L-phenylalanine is a specialized amino acid derivative featuring both N-methylation and a 3-methoxy substitution on the aromatic ring, protected by a 9-fluorenylmethyloxycarbonyl (Fmoc) group. As a non-standard, synthetically modified amino acid, it plays a significant role in advanced peptide chemistry and related biochemical research. The unique structural modifications confer distinct steric and electronic properties, making this compound a valuable tool for researchers seeking to manipulate peptide conformation, stability, and bioactivity. Its incorporation into peptides or other biopolymers can yield insights into structure-activity relationships and facilitate the design of novel biomolecules with tailored properties.
Peptide Synthesis: In solid-phase peptide synthesis (SPPS), N-Fmoc-N-methyl-3-methoxy-L-phenylalanine serves as a protected building block for the incorporation of N-methylated and methoxy-substituted phenylalanine residues. The Fmoc group allows for efficient stepwise assembly under mild deprotection conditions, while the N-methylation can disrupt backbone hydrogen bonding, influencing secondary structure formation. Introduction of this derivative enables the synthesis of peptides with enhanced conformational rigidity, resistance to enzymatic degradation, or altered receptor affinity, supporting the development of peptidomimetics and bioactive analogs.
Structure-Activity Relationship Studies: The presence of both N-methyl and 3-methoxy modifications in this amino acid analog provides a means to systematically probe the effects of steric hindrance and electronic alterations on peptide function. Incorporating it into peptide libraries or specific sequences allows researchers to investigate how these modifications impact biological activity, receptor binding, or protein-protein interactions. Such studies are essential for optimizing ligand design and understanding the determinants of molecular recognition.
Conformational Analysis: The distinctive features of N-methylated and methoxy-substituted amino acids make them valuable for exploring peptide backbone dynamics and conformational preferences. By restricting certain dihedral angles and modulating side chain interactions, this compound aids in the elucidation of folding patterns, helix propensity, and turn formation in synthetic and natural peptides. Researchers utilize these properties to model constrained peptides or to design scaffolds for structural biology investigations.
Peptidomimetic Development: The strategic use of N-Fmoc-N-methyl-3-methoxy-L-phenylalanine in peptide analogs supports the creation of peptidomimetics with improved pharmacokinetic profiles or target selectivity. The introduction of N-methyl groups can increase metabolic stability and membrane permeability, while the methoxy substituent provides further opportunities for tuning hydrophobicity and electronic interactions. These features are exploited in the design of novel molecular probes, enzyme inhibitors, or receptor modulators for biochemical and pharmaceutical research.
Analytical Method Development: Incorporation of this amino acid derivative into synthetic standards or model peptides facilitates the calibration and validation of analytical techniques such as HPLC, mass spectrometry, and NMR spectroscopy. The unique chemical shifts and fragmentation patterns associated with its structural modifications provide reliable markers for method optimization and compound identification. Analytical chemists leverage these properties to ensure accurate detection and quantification of modified peptides in complex mixtures or during quality control processes.
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