N-Fmoc-N-methyl-O-(3-methylbutyl)-L-serine is an alkylated, N-methylated serine derivative with altered polarity and sterics. The residue is used to probe hydrogen-bond disruption and side-chain packing. Researchers employ it in designing membrane-active or hydrophobicity-tuned peptides. Its protected groups support orthogonal synthesis.
CAT No: R2122
CAS No:2255321-12-9
Synonyms/Alias:N-Fmoc-N-methyl-O-(3-methylbutyl)-L-Serine;2255321-12-9;SCHEMBL21837547;CS-0439335;G81912;N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-isopentyl-N-methyl-L-serine;
N-Fmoc-N-methyl-O-(3-methylbutyl)-L-Serine is a specialized amino acid derivative designed for advanced peptide synthesis applications. Featuring an N-terminal fluorenylmethyloxycarbonyl (Fmoc) protecting group, an N-methyl modification, and a unique O-alkylation with a 3-methylbutyl moiety, this compound offers distinct steric and electronic properties that expand the toolkit available for custom peptide engineering. Its structural modifications facilitate the incorporation of non-canonical residues into peptide chains, enabling researchers to explore novel backbone conformations, modulate peptide function, and interrogate structure-activity relationships. The compound's utility is particularly significant in the context of synthetic peptide chemistry, combinatorial library construction, and the development of peptide-based biomaterials.
Peptide Synthesis: In solid-phase peptide synthesis (SPPS), this Fmoc-protected serine analog serves as a valuable building block for introducing N-methyl and O-alkyl functionalities into peptide sequences. These modifications are known to enhance peptide stability, influence secondary structure, and modulate bioactive properties. The compound's compatibility with standard Fmoc/tBu protocols allows for efficient coupling and deprotection cycles, supporting the assembly of complex peptides with site-specific modifications that are challenging to achieve using canonical amino acids alone.
Backbone Conformation Studies: The presence of both N-methylation and O-alkylation in this derivative offers a powerful tool for researchers investigating peptide backbone dynamics. Incorporation of such residues can restrict conformational flexibility, providing insights into the role of backbone modifications in protein folding, helix formation, and β-turn induction. This enables systematic exploration of the relationship between backbone structure and peptide function, which is essential for the rational design of foldamers and conformationally constrained peptides.
Peptidomimetic Design: The unique structural features of N-Fmoc-N-methyl-O-(3-methylbutyl)-L-Serine make it highly relevant for the synthesis of peptidomimetics—molecules that mimic the structure and function of peptides but possess enhanced resistance to enzymatic degradation. By introducing sterically bulky and electronically distinct side chains, researchers can tailor molecular recognition, binding affinity, and pharmacokinetic properties in peptide analogs. This approach is particularly valuable in the development of research tools for probing protein-protein interactions and in the creation of peptide-based probes for biochemical assays.
Combinatorial Library Construction: The compound's compatibility with automated peptide synthesizers and its amenability to high-throughput protocols make it suitable for generating diverse peptide libraries. These libraries are instrumental in screening for novel ligands, enzyme substrates, or receptor modulators. The ability to systematically vary side chain and backbone modifications within library members facilitates the identification of peptides with optimized activity profiles, specificity, or stability for research and discovery purposes.
Analytical Method Development: The use of non-natural amino acid derivatives such as this one can aid in the development and validation of analytical methodologies for peptide characterization. Its unique mass and chromatographic properties provide internal standards or reference points in techniques such as liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance (NMR) spectroscopy. This supports accurate identification, quantitation, and purity assessment of synthetic peptides, thereby enhancing the reliability of peptide-based research workflows.
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