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 synthetic amino acid derivative widely utilized in peptide chemistry and advanced biochemical research. As a modified form of L-serine, this compound features both N-methylation and O-methylation, along with an N-terminal 9-fluorenylmethyloxycarbonyl (Fmoc) protecting group. These structural modifications confer unique chemical properties, making the molecule an essential tool for the synthesis of specialized peptides and the exploration of structure-activity relationships. Its distinctive profile enables researchers to introduce steric and electronic effects at specific positions within peptide chains, thereby expanding the possibilities for designing novel biomolecules with tailored functionalities.
Peptide Synthesis: In the field of solid-phase peptide synthesis (SPPS), N-Fmoc-N,O-dimethyl-L-serine serves as a valuable building block for the incorporation of methylated serine residues into peptide sequences. The Fmoc group provides temporary protection of the amino terminus, allowing for selective deprotection and sequential coupling, while the N- and O-methyl groups prevent undesired side reactions and enhance the stability of the serine moiety. Incorporation of this derivative enables the generation of peptides with increased resistance to enzymatic degradation and altered conformational properties, supporting the development of bioactive analogs and peptidomimetics.
Conformational Studies: The introduction of N- and O-methyl groups into serine residues is a strategic approach for probing peptide backbone flexibility and side-chain interactions. Use of this dimethylated serine derivative allows researchers to systematically investigate the influence of steric hindrance and hydrogen-bonding disruption on peptide secondary structure. Such studies are critical for elucidating the structural determinants of protein folding, stability, and molecular recognition, particularly in the context of α-helices, β-sheets, and turn motifs.
Protease Resistance Research: Modified amino acids like N-Fmoc-N,O-dimethyl-L-serine are frequently employed to enhance the metabolic stability of synthetic peptides. The methylation of both the nitrogen and oxygen atoms in the serine side chain significantly impedes proteolytic cleavage at susceptible sites. Incorporating this residue into peptide sequences enables the design of analogs with improved resistance to enzymatic hydrolysis, facilitating studies on peptide persistence, bioavailability, and degradation pathways in vitro.
Structure-Activity Relationship (SAR) Exploration: By substituting canonical serine with its N,O-dimethylated counterpart, researchers can systematically assess the impact of side-chain modifications on biological activity. This approach is instrumental in SAR studies, where the goal is to correlate specific chemical modifications with changes in receptor binding, enzymatic activity, or cellular uptake. The use of this methylated serine derivative thus supports the rational design of peptides with optimized functional properties for biochemical assays and mechanistic investigations.
Analytical Method Development: The unique physicochemical characteristics of N-Fmoc-N,O-dimethyl-L-serine make it a useful standard or internal reference in chromatographic and mass spectrometric analyses. Its defined mass and modified structure assist in method validation, calibration, and the evaluation of derivatization protocols in peptide analysis workflows. Use of this compound in analytical development ensures accurate identification, quantification, and quality control of methylated serine-containing peptides and related biomolecules.
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