N-Fmoc-N,O-dimethyl-L-serine is a serine analog with methylated nitrogen and oxygen functionalities that alter hydrogen bonding. The residue supports synthetic exploration of steric and electronic effects in peptides. Researchers use it to examine backbone constraints and side-chain interactions. Its protections enable controlled incorporation into modified peptides.
CAT No: R2161
CAS No:1569103-64-5
Synonyms/Alias:N-Fmoc-N,O-dimethyl-L-serine;1569103-64-5;(2S)-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]-3-methoxypropanoic acid;N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N,O-dimethyl-L-serine;(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl](methyl)amino}-3-methoxypropanoic acid;N-((9H-fluoren-9-ylmethoxy)carbonyl)-N,O-dimethyl-L-Serine;SCHEMBL25186418;MFCD31730320;HY-W039102;DA-65745;CS-0096677;D75760;A929555;(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}(methyl)amino)-3-methoxypropanoic acid;
N-Fmoc-N,O-dimethyl-L-serine is a specialized, synthetically modified amino acid derivative frequently utilized in peptide chemistry and organic synthesis. Characterized by its N-terminal 9-fluorenylmethyloxycarbonyl (Fmoc) protection and dual methylation on both the nitrogen and oxygen atoms of the serine residue, this compound offers enhanced chemical stability and unique reactivity profiles. The methylation of both the amino and hydroxyl groups serves to modulate the molecule's electronic and steric environment, facilitating selective transformations and minimizing side reactions during peptide assembly. Its compatibility with solid-phase peptide synthesis (SPPS) protocols, as well as its ability to introduce site-specific modifications, makes it a valuable tool for researchers seeking to design complex peptide architectures or study structure-activity relationships in modified peptides.
Peptide Synthesis: As a key building block in peptide synthesis, N-Fmoc-N,O-dimethyl-L-serine is widely employed to introduce methylated serine residues into peptide chains. The Fmoc protection allows for efficient stepwise elongation using Fmoc-based SPPS, while the N,O-dimethylation protects the serine side chain from undesired acylation or side reactions, particularly O-acylation, which can otherwise complicate purification and yield. Researchers leverage this compound to generate peptides with enhanced backbone rigidity and altered hydrogen-bonding patterns, which can be critical for studying conformational preferences or developing peptides with improved metabolic stability and bioactivity in biochemical assays.
Peptidomimetic Design: The unique steric and electronic properties imparted by the dimethylation of serine make this derivative a strategic choice for the synthesis of peptidomimetics. By substituting canonical serine with its N,O-dimethyl analog, scientists can disrupt traditional hydrogen-bonding networks and modulate peptide secondary structure, thereby mimicking or antagonizing the function of natural peptides. This approach is particularly valuable in the development of enzyme inhibitors, receptor ligands, or substrates for probing protein-peptide interactions, as the methyl groups can enhance resistance to proteolytic degradation and alter recognition profiles.
Chemical Biology Probes: In chemical biology, N-Fmoc-N,O-dimethyl-L-serine is incorporated into peptides or small molecules to serve as a functional probe for investigating post-translational modifications or protein-ligand interactions. The methyl groups can mimic naturally occurring methylation patterns or serve as chemical tags that alter the interaction landscape of the modified peptide. By incorporating this compound into synthetic peptides, researchers can study the effects of serine methylation on protein recognition, signaling pathways, or enzyme activity, providing insights into the regulatory mechanisms of methylation in biological systems.
Conformational Constraint Studies: The introduction of N,O-dimethylserine residues into peptide backbones is a powerful strategy for exploring conformational constraints and the resulting effects on peptide structure and function. The dual methylation restricts the flexibility of the serine side chain, promoting specific backbone conformations and potentially stabilizing secondary structures such as β-turns or helices. This property is exploited in the design of peptides with defined three-dimensional structures for structural biology studies, as well as in the development of scaffolds for molecular recognition and catalysis.
Material Science Applications: Beyond traditional biochemical research, N-Fmoc-N,O-dimethyl-L-serine finds utility in material science, particularly in the design of peptide-based materials and nanostructures. The presence of methylated serine residues can influence the self-assembly properties of peptides, leading to the formation of novel hydrogels, nanofibers, or supramolecular architectures with tailored mechanical and chemical properties. Researchers use this derivative to modulate peptide-peptide interactions, control solubility, or introduce functional handles for further chemical modification, expanding the scope of peptide-based materials for applications in biomaterials, drug delivery, and tissue engineering. The versatility and chemical robustness of N-Fmoc-N,O-dimethyl-L-serine thus make it an indispensable reagent for advancing research at the interface of chemistry, biology, and materials science.
2. The spatiotemporal control of signalling and trafficking of the GLP-1R
3. TMEM16F and dynamins control expansive plasma membrane reservoirs
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