英文名称:Fmoc-N-methyl-L-valine英文同义词:N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-N-methyl-L-valine;(9H-Fluoren-9-yl)MethOxy]Carbonyl N-Me-Val-OH;Fmoc-N-Me-Val-OH (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-methylbutanoic acid;FMOC-MEVAL-OH;FMOC-N-ALPHA-METHYL-L-VALINE;FMOC-N-ME-VALINE;FMOC-N-ME-VAL-OH;FMOC-N-METHYL-L-VALINECAS号:84000-11-3分子式:C21H23NO4分子量:353.41EINECS号:Mol文件:84000-11-3.mol
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Fmoc-N-Me-Val-OH, chemically known as Fmoc-N-methylvaline, is a specialized protected amino acid derivative widely utilized in modern peptide synthesis. Its molecular formula is C19H27NO5, and it carries the CAS registry number 146386-04-7. This compound serves as a critical building block for the solid-phase peptide synthesis (SPPS) of complex therapeutic peptides and peptidomimetics. The structure features an N-terminal fluorenylmethyloxycarbonyl (Fmoc) protecting group, which ensures stability during synthesis and allows for selective deprotection under mild basic conditions, typically using piperidine. Simultaneously, the alpha-amino nitrogen is methylated, introducing a steric constraint that significantly alters the conformational properties of the resulting peptide chain.
The primary application of Fmoc-N-Me-Val-OH lies in the design of protease-resistant peptides. By incorporating an N-methylated valine residue, researchers can disrupt standard secondary structures like alpha-helices or beta-sheets, thereby enhancing metabolic stability against enzymatic degradation in biological systems. This modification is particularly valuable in developing drugs targeting G-protein coupled receptors (GPCRs), ion channels, and enzymes where specific structural rigidity is required for high-affinity binding. Furthermore, the bulky Fmoc group facilitates purification processes by preventing premature side reactions during coupling steps. In pharmaceutical research, this reagent enables the construction of cyclic peptides and constrained analogs with improved pharmacokinetic profiles. It is also instrumental in fragment-based drug discovery, allowing scientists to explore diverse chemical space efficiently. Due to its high purity and stability, Fmoc-N-Me-Val-OH is a preferred choice for academic laboratories and industrial biotechnology firms aiming to synthesize novel bioactive molecules with optimized biological activity and reduced toxicity. Its versatility makes it indispensable in advancing next-generation peptide therapeutics.