Fmoc-L-MeSer(tBu)-OH is an Fmoc-protected, amino-acid derivative of L-serine bearing an N-terminal fluorenylmethoxycarbonyl (Fmoc) protecting group and a side-chain modification where the β-hydroxyl is methylated (Me) and the hydroxyl is further protected as a tert-butyl ether (tBu). The molecule contains a free carboxylic acid and an Fmoc-protected amino group, with the serine-derived β-carbon bearing the substituted hydroxyl functionality masked by the tert-butyl group to control chemoselectivity during peptide assembly. In peptide chemistry, it functions as a protected building block for incorporating a methylated, tert-butyl-protected serine analogue into peptide chains via stepwise coupling while the Fmoc group supports orthogonal deprotection and the side-chain protection helps minimize side reactions of the hydroxyl during synthesis.
CAT No: CP25536
CAS No:197632-77-2
Synonyms/Alias:197632-77-2;Fmoc-N-Me-Ser(tBu)-OH;N-Fmoc-N-Methyl-O-tert-butyl-L-serine;MFCD02094430;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-(tert-butoxy)propanoicacid;PubChem19046;TMA040;SCHEMBL15083399;CTK3J1822;MolPort-006-701-287;Fmoc-N-methyl-O-t-butyl-L-serine;ZINC2389703;ANW-74596;CF-496;Fmoc-N-methyl-O-tert-butyl-L-serine;AKOS015837171;AKOS015908481;AM84674;AN-7893;CS13894;MP-0545;RTR-009167;AJ-35605;AK-41517;SC-24299
Fmoc-L-MeSer(tBu)-OH is a chiral, N-Fmoc-protected methionine-derived serine analog in which the amino acid backbone is masked as an Fmoc carbamate for orthogonal peptide coupling, while the side-chain oxygen is protected as a tert-butyl ether. The molecule contains the stereogenic center at the alpha carbon of the L-configuration, a carboxylic acid handle for C-terminal activation, and a protected hydroxyl group that can be selectively deprotected under acid-labile conditions to reveal a reactive serine-like alcohol. The tert-butyl protection on the side-chain hydroxyl provides stability during standard peptide assembly chemistries and enables subsequent functionalization of the side-chain oxygen for phosphorylation mimics, glycosylation, or linkage formation. The presence of both the Fmoc group and acid-labile tBu ether makes the compound a practical protected amino acid derivative for building block preparation and downstream synthetic modification in peptide science and process-oriented peptide intermediate manufacture.
1. Peptide Synthesis
Fmoc-L-MeSer(tBu)-OH is used as an Fmoc-protected amino acid building block for solid-phase peptide synthesis and related solution-phase peptide coupling workflows. The Fmoc carbamate on the nitrogen supports base-mediated deprotection to expose the free amine for iterative coupling, while the carboxylic acid enables activation for amide bond formation with incoming residues. The side-chain tert-butyl ether protects a serine-like hydroxyl from undesired acylation or side reactions during chain assembly, preserving chemoselectivity for later deprotection. The resulting peptide products can incorporate the protected MeSer residue as a chemically defined stereocenter-bearing unit, supporting synthesis of peptide libraries and sequence-specific analogs used in biochemical research and synthetic methodology development.
2. Side-Chain Functionalization
Fmoc-L-MeSer(tBu)-OH supports side-chain functionalization strategies where controlled unveiling of the protected hydroxyl is required after peptide assembly or intermediate construction. The tert-butyl-protected alcohol can be removed to generate a reactive hydroxyl that participates in esterification, etherification, or conjugation chemistry, enabling installation of linkers for bioconjugation or incorporation of functional motifs such as phosphorylation mimics. The Fmoc-protected backbone architecture allows the compound to be handled and coupled without premature side-chain reactivity, improving compatibility with diverse coupling reagents and protecting-group schemes. Downstream derivatives may serve as peptide-based scaffolds for chemical biology studies, molecular recognition probes, or intermediate materials for fine chemical synthesis where oxygen functional group placement is a key design element.
3. Chemical Biology Probes
Fmoc-L-MeSer(tBu)-OH is applied in chemical biology research to generate peptide and peptidomimetic probes that require a protected hydroxyl for controlled post-synthetic modification. The L-stereochemistry at the alpha carbon and the serine-like side-chain oxygen enable incorporation into recognition motifs where stereodefined geometry and hydrogen-bonding capacity can influence binding or labeling behavior in assay formats. The Fmoc strategy provides orthogonal control over N-deprotection, while the tBu ether enables timing of side-chain activation to match labeling schedules or conjugation steps. Synthesized probe constructs can then be used as defined molecular tools for studying biomolecular interactions, mapping binding determinants, or preparing labeled peptide standards for analytical and mechanistic investigations.
4. Peptidomimetics And SAR Studies
Fmoc-L-MeSer(tBu)-OH can be employed in peptidomimetic and structure-activity relationship studies where substitution of a hydroxyl-bearing residue with a protected, stereodefined analog supports systematic scaffold variation. The protected hydroxyl functionality serves as a handle for generating analogs with altered polarity, hydrogen-bonding patterns, or attachment points, while the Fmoc-protected amine ensures reliable incorporation into peptide-like frameworks. The ability to deprotect the side-chain oxygen after assembly allows rapid generation of derivative series for SAR workflows, including oxygen functional group transformations that modulate conformational preferences. The compound thus functions as a chiral amino acid intermediate that supports medicinal chemistry-style library construction and downstream analytical evaluation of structure-dependent properties.
5. Pharmaceutical Manufacturing Intermediates
Fmoc-L-MeSer(tBu)-OH is suitable for pharmaceutical manufacturing supply chains that require protected amino acid intermediates compatible with scalable peptide synthesis operations. The Fmoc group provides a robust N-protection strategy for stepwise peptide assembly, and the acid-labile tert-butyl ether on the side-chain hydroxyl supports predictable deprotection sequencing during downstream processing and purification. The presence of a free carboxylic acid enables consistent conversion to activated forms for coupling under controlled manufacturing conditions, aligning with industrial peptide intermediate preparation practices. The resulting protected residue incorporation can support production of defined peptide intermediates and reference materials used in process development and quality-relevant synthetic route design within industrial chemical manufacturing contexts.
6. Process Chemistry And Fine Chemical Synthesis
Fmoc-L-MeSer(tBu)-OH serves as a chiral intermediate for process chemistry and fine chemical synthesis routes that rely on orthogonal protection to manage functional group reactivity. The combination of base-labile Fmoc and acid-labile tBu ether allows chemists to stage deprotections and derivatizations while maintaining the integrity of the stereocenter and the carboxyl functionality during intermediate handling. The protected hydroxyl can be selectively revealed to enable controlled formation of oxygen-linked derivatives, including ester and ether intermediates used for further transformations beyond peptide contexts. The compound's protected-amino-acid framework therefore supports manufacturing-friendly planning of downstream synthetic steps, including preparation of functionalized amino acid derivatives and peptide-derived intermediates for specialty chemical production.
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