Fmoc-N-Me-Ala-OH, an N-Fmoc-N-methyl amino acid, is available for the peptide-coupling reaction.
CAT No: R1359
CAS No:84000-07-7
Synonyms/Alias:Fmoc-N-Me-Ala-OH;84000-07-7;Fmoc-N-methyl-L-alanine;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)propanoicacid;Fmoc-Nalpha-methyl-L-alanine;MFCD00153384;(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl](methyl)amino}propanoicacid;(2S)-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]propanoicacid;Fmoc-L-MeAla-OH;AmbotzFAA1395;AC1LEMGZ;PubChem18933;Fmoc-N-Methyl-Ala-OH;Fmoc-N-a-methyl-L-alanine;47594_ALDRICH;SCHEMBL120596;47594_FLUKA;CTK7I3107;ZINC57597;MolPort-003-934-200;ANW-37736;CF-309;SBB067205;AKOS015907196;AN-7887
Fmoc-N-Me-Ala-OH, also known as N-α-Fmoc-N-methyl-L-alanine, is a protected, non-proteinogenic amino acid derivative widely utilized in modern peptide synthesis. Featuring an N-terminal 9-fluorenylmethoxycarbonyl (Fmoc) protecting group and a methylated amide nitrogen, this compound is especially valued for its ability to introduce N-methylated residues into synthetic peptides. The presence of the N-methyl modification imparts unique conformational and physicochemical properties to peptides, influencing secondary structure, biological stability, and resistance to enzymatic degradation. As such, Fmoc-N-Me-Ala-OH serves as a critical building block for researchers seeking to engineer peptides with enhanced pharmacological or biophysical characteristics.
Peptide Synthesis: Fmoc-N-Me-Ala-OH is primarily employed in solid-phase peptide synthesis (SPPS) protocols to generate peptides containing N-methylated alanine residues. The Fmoc group provides orthogonal protection, allowing for efficient stepwise assembly of complex sequences while minimizing side reactions. Incorporation of N-methylalanine can modulate backbone conformation, restrict peptide flexibility, and enhance resistance to proteolytic cleavage, making it a preferred choice for synthesizing bioactive peptides, peptidomimetics, and cyclic peptides with improved metabolic stability.
Structural and Conformational Studies: The methylation of the amide nitrogen in N-methylalanine introduces steric and electronic effects that significantly impact peptide secondary structure. Researchers utilize this derivative to probe the influence of backbone N-methylation on helix, sheet, and turn formation within peptides and proteins. By strategically incorporating Fmoc-N-Me-Ala-OH into model systems, investigators can dissect the role of N-methylation in modulating hydrogen bonding patterns, folding kinetics, and overall molecular architecture, thereby advancing the understanding of peptide structure-function relationships.
Design of Peptidomimetics: The unique properties of N-methylated amino acids are exploited in the rational design of peptidomimetic compounds. By integrating N-methylalanine residues, scientists can develop peptide analogues with enhanced membrane permeability, improved oral bioavailability, and increased resistance to enzymatic hydrolysis. Fmoc-N-Me-Ala-OH is thus a valuable synthetic tool for medicinal chemistry and chemical biology applications, enabling the creation of novel scaffolds that mimic natural peptides but possess optimized pharmacokinetic and pharmacodynamic profiles.
Development of Protease-Resistant Sequences: Incorporation of N-methylalanine via Fmoc-N-Me-Ala-OH is a well-established strategy for enhancing the proteolytic stability of synthetic peptides. N-methylation disrupts the recognition and cleavage sites of many proteases, thereby prolonging peptide half-life in biological environments. This property is particularly beneficial in the development of research-grade peptides intended for challenging applications, such as those involving extended exposure to proteolytic enzymes or harsh assay conditions.
Analytical Method Development: The unique chromatographic and spectroscopic signatures of N-methylated residues make Fmoc-N-Me-Ala-OH a useful standard in the development and validation of analytical methods for peptide characterization. Its incorporation facilitates the optimization of separation protocols, mass spectrometric detection, and structural elucidation techniques. Analytical chemists leverage these features to improve the accuracy and reliability of peptide quality control, purity assessment, and structural confirmation workflows.
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