N-Fmoc-N-methyl-4-phenyl-L-phenylalanine is a highly aromatic amino acid analog with enhanced hydrophobic bulk. The N-methyl group restricts backbone flexibility, aiding studies of helix stabilization and aromatic stacking. Researchers use it to construct rigid peptide frameworks. Its profile supports advanced structural engineering.
CAT No: R2121
CAS No:696615-48-2
Synonyms/Alias:696615-48-2;Fmoc-MeBph-OH;N-Fmoc-N-methyl-4-phenyl-L-phenylalanine;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-([1,1'-biphenyl]-4-yl)propanoic acid;Fmoc-L-MeBip-OH;MFCD31657297;(2S)-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]-3-(4-phenylphenyl)propanoic acid;F80977;[1,1'-Biphenyl]-4-propanoic acid, |A-[[(9H-fluoren-9-ylmethoxy)carbonyl]methylamino]-, (|AS)-;
N-Fmoc-N-methyl-4-phenyl-L-phenylalanine is a synthetic amino acid derivative characterized by the presence of an N-terminal 9-fluorenylmethyloxycarbonyl (Fmoc) protecting group and an N-methyl modification on the amine. Featuring a phenyl group at the para position of the phenylalanine side chain, this compound is specifically engineered for advanced peptide synthesis applications. Its unique structural modifications confer steric and electronic properties that are highly valued in the design of bioactive peptides, peptidomimetics, and structurally constrained analogs. Researchers in the fields of medicinal chemistry, chemical biology, and peptide engineering frequently utilize such derivatives to overcome synthetic challenges and to introduce novel functional attributes into peptide frameworks.
Peptide Synthesis: As a specialized building block, N-Fmoc-N-methyl-4-phenyl-L-phenylalanine is widely employed in solid-phase peptide synthesis (SPPS) protocols. The Fmoc group provides orthogonal protection compatible with contemporary peptide synthesis strategies, allowing for efficient stepwise assembly and deprotection. The N-methylation of the amine not only introduces conformational rigidity but also imparts resistance to enzymatic degradation, making it a valuable component in the synthesis of peptides with enhanced metabolic stability and defined secondary structure.
Peptidomimetic Design: Incorporation of this N-methylated, para-phenyl-substituted phenylalanine analog is instrumental in the development of peptidomimetics. Its structural features disrupt conventional backbone hydrogen bonding patterns, thereby modulating peptide folding and bioactive conformations. Researchers exploit these properties to design ligands, inhibitors, and molecular probes with improved receptor selectivity, binding affinity, and proteolytic resistance, which are critical for probing biological pathways and validating therapeutic targets in vitro.
Structure-Activity Relationship Studies: The unique chemical profile of this amino acid derivative makes it an excellent probe for structure-activity relationship (SAR) investigations. By systematically substituting native phenylalanine residues with the modified analog, scientists can assess the impact of N-methylation and aromatic substitution on peptide function, receptor interaction, and molecular recognition. Such studies are essential for optimizing peptide-based lead compounds and elucidating the determinants of biological activity.
Conformational Constraint Engineering: N-methylation and para-phenyl substitution together provide a means to restrict backbone flexibility and side-chain orientation in synthetic peptides. This property is leveraged to stabilize specific secondary structures such as β-turns and helices, which are often required for biological function or for mimicking protein-protein interaction motifs. The use of this compound enables precise control over peptide folding, facilitating the design of conformationally preorganized scaffolds for research in protein engineering and biomolecular design.
Analytical Method Development: The distinct chromophoric and structural characteristics of N-Fmoc-N-methyl-4-phenyl-L-phenylalanine make it a useful reference compound in the development and validation of analytical methods for peptide-based products. Its defined UV absorbance and chromatographic behavior assist in the calibration of HPLC, mass spectrometry, and other analytical platforms, supporting rigorous quality control and characterization of synthetic peptides in research and manufacturing environments.
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