N-Fmoc-(S)-3-(methylamino)butanoic acid features a branched chain with a secondary amine that affects charge and conformational behavior. The residue supports studies of backbone flexibility, hydrogen bonding, and steric modulation. Researchers use it to design functionally constrained peptide segments. Its protection scheme ensures reliable solid-phase coupling.
CAT No: R2151
CAS No:882183-85-9
Synonyms/Alias:N-Fmoc-(S)-3-(methylamino)butanoic acid;882183-85-9;(3S)-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}(methyl)amino)butanoic acid;(3S)-3-{[(9H-fluoren-9-ylmethoxy)carbonyl](methyl)amino}butanoic acid;N-Fmoc-(S)-3-(methylamino)butanoicacid;CS-0181036;F80936;EN300-22847242;(3S)-3-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]butanoic acid;(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)butanoic acid;
N-Fmoc-(S)-3-(methylamino)butanoic acid is a specialized carbohydrate-derived building block frequently utilized in peptide synthesis and medicinal chemistry. Featuring a protected amino group via the fluorenylmethyloxycarbonyl (Fmoc) moiety and a distinctive methylamino substitution, this compound enables chemists to introduce site-specific modifications and structural diversity into peptide chains. Its chiral center ensures stereochemical fidelity, making it valuable for constructing peptides and peptidomimetics with precise biological activity. The stability of the Fmoc group under basic conditions and its facile removal using mild bases provide synthetic flexibility, while the methylamino functionality imparts unique conformational and electronic properties to the resulting molecules. As such, N-Fmoc-(S)-3-(methylamino)butanoic acid serves as a versatile intermediate in advanced organic synthesis, enabling the exploration of novel molecular architectures for research and development.
Peptide Synthesis: In solid-phase peptide synthesis (SPPS), N-Fmoc-(S)-3-(methylamino)butanoic acid is incorporated as a non-standard amino acid to create peptides with enhanced stability, altered backbone conformations, or improved pharmacological profiles. The Fmoc protection ensures compatibility with standard SPPS protocols, allowing for sequential coupling and deprotection steps without compromising the integrity of the methylamino group. Researchers leverage this compound to introduce steric bulk or modulate the hydrogen bonding network within peptide sequences, facilitating the design of bioactive peptides with tailored properties for biochemical studies.
Peptidomimetic Design: The methylamino-substituted butanoic acid backbone of this compound is instrumental in the synthesis of peptidomimetics—molecules that mimic the structure and function of peptides but exhibit improved metabolic stability or membrane permeability. By replacing conventional amino acids with this analog, scientists can probe structure-activity relationships and optimize lead compounds for target engagement. Its unique side chain offers opportunities to disrupt peptide secondary structures, such as alpha-helices or beta-sheets, enabling the rational design of inhibitors or modulators for protein-protein interactions.
Combinatorial Chemistry: N-Fmoc-(S)-3-(methylamino)butanoic acid is frequently employed in combinatorial chemistry approaches, where its incorporation into diverse libraries expands the chemical space available for screening. The methylamino group introduces a distinct electronic and steric profile, increasing the likelihood of identifying novel bioactive compounds. Automated synthesis platforms benefit from the Fmoc protection, which streamlines the assembly of large compound libraries for high-throughput screening campaigns in drug discovery or chemical biology.
Structural Biology Probes: This Fmoc-protected amino acid analog is valuable for generating structural probes that elucidate protein folding, dynamics, or interactions. Site-specific incorporation of the methylamino functionality enables researchers to introduce spectroscopic or isotopic labels, facilitating NMR or fluorescence studies. Its presence can also modulate local conformational preferences, providing insights into the structural determinants of biomolecular recognition or catalysis.
Chemical Biology Tools: The unique properties of N-Fmoc-(S)-3-(methylamino)butanoic acid make it a useful precursor for the development of chemical biology tools. By leveraging its reactivity and compatibility with a variety of coupling strategies, scientists can synthesize modified peptides or small molecules that serve as probes, affinity tags, or molecular switches. These tools are instrumental in dissecting cellular pathways, mapping protein interactions, or validating drug targets in complex biological systems.
Research and Development of Novel Therapeutics: The incorporation of this methylamino-substituted building block into peptide-based scaffolds supports the exploration of new therapeutic modalities. Its structural features enable the fine-tuning of peptide conformation, stability, and bioavailability, which are critical parameters in the preclinical evaluation of drug candidates. Research teams utilize it to generate diverse analogs for structure-activity relationship studies, ultimately accelerating the identification and optimization of promising leads for further investigation.
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