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 amino acid derivative featuring an N-terminal 9-fluorenylmethyloxycarbonyl (Fmoc) protecting group and a methylamino substitution on the butanoic acid backbone. As a non-canonical, chiral amino acid analog, it is primarily utilized in peptide synthesis and research involving modified peptides. Its unique structural attributes offer valuable opportunities for the design of peptides with altered backbone conformations or side chain functionalities, making it a critical building block in the development of novel biomolecules and advanced biochemical tools.
Peptide Synthesis: The compound serves as a protected amino acid monomer in solid-phase peptide synthesis (SPPS), where the Fmoc group enables selective N-terminal protection and deprotection cycles. Its methylamino substitution introduces a non-standard side chain into peptide sequences, facilitating the generation of peptides with enhanced conformational constraints or altered physicochemical properties. Researchers leverage this feature to probe structure-activity relationships or to design peptides with improved stability, binding affinity, or resistance to enzymatic degradation.
Peptidomimetic Design: Incorporation of N-Fmoc-(S)-3-(methylamino)butanoic acid into peptide frameworks supports the synthesis of peptidomimetics—molecules that mimic the structure and function of natural peptides but with increased metabolic stability or novel bioactivity profiles. The methylamino group can introduce steric and electronic modifications, allowing fine-tuning of peptide backbone conformation and side chain interactions. This approach is particularly valuable in the creation of peptide-based probes, enzyme inhibitors, or molecular recognition elements for biochemical assays.
Structure-Activity Relationship (SAR) Studies: The compound is instrumental in SAR investigations aimed at understanding the influence of backbone and side chain modifications on peptide function. By substituting standard amino acids with this methylamino analog, researchers can systematically explore how such changes affect biological activity, receptor binding, or molecular recognition. These insights are critical for rational peptide design and optimization in both fundamental research and applied biotechnology.
Conformational Analysis: Due to its unique stereochemistry and side chain features, N-Fmoc-(S)-3-(methylamino)butanoic acid is employed in studies focused on peptide folding, secondary structure formation, and backbone dynamics. The presence of the methylamino group can restrict local conformational flexibility, making it a useful tool for elucidating the structural determinants of peptide stability and function. Such research advances the understanding of protein folding principles and aids in the engineering of peptides with desired structural attributes.
Analytical Method Development: The compound is also used as a reference standard or model substrate in the development and validation of analytical techniques for peptide and amino acid derivatives. Its distinct chemical structure and Fmoc protection facilitate method optimization in high-performance liquid chromatography (HPLC), mass spectrometry, and related analytical platforms. These applications support quality control, purity assessment, and structural characterization in peptide synthesis workflows and analytical laboratories.
1. Cationic cell-penetrating peptides are potent furin inhibitors
2. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
3. Immune-awakening Saccharomyces-inspired nanocarrier for oral target delivery to lymph and tumors
4. Myotropic activity of allatostatins in tenebrionid beetles
If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at . We will endeavor to provide highly satisfying products and services.
Creative Peptides is a trusted CDMO partner specializing in high-quality peptide synthesis, conjugation, and manufacturing under strict cGMP compliance. With advanced technology platforms and a team of experienced scientists, we deliver tailored peptide solutions to support drug discovery, clinical development, and cosmetic innovation worldwide.
From custom peptide synthesis to complex peptide-drug conjugates, we provide flexible, end-to-end services designed to accelerate timelines and ensure regulatory excellence. Our commitment to quality, reliability, and innovation has made us a preferred partner across the pharmaceutical, biotechnology, and personal care industries.
Read More