Description

(R)-N-Fmoc-alpha-methylasparagine (CAS: 1403590-50-0) is a high-purity, chiral amino acid derivative designed for advanced peptide synthesis and pharmaceutical research. With the molecular formula C₂₀H₂₀N₂O₅, this compound features an Fmoc-protected alpha-methylated asparagine side chain, offering enhanced steric control and stability in solid-phase peptide synthesis (SPPS). Its IUPAC name, (2R)-4-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methyl-4-oxobutanoic acid, reflects its precise stereochemistry, critical for maintaining peptide conformation and biological activity. Ideal for researchers developing constrained peptides or peptidomimetics, this product is rigorously tested via HPLC and NMR to ensure ≥95% purity, meeting stringent standards for drug discovery and biochemical studies. Supplied as a white to off-white powder, it is stored under inert conditions to preserve reactivity.

Properties

• CAS Number: 1403590-50-0
• Complexity: 573
• IUPAC Name: (2R)-4-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methyl-4-oxo-butanoic acid
• InChI: InChI=1S/C20H20N2O5/c1-20(18(24)25,10-17(21)23)22-19(26)27-11-16-14-8-4-2-6-12(14)13-7-3-5-9-15(13)16/h2-9,16H,10-11H2,1H3,(H2,21,23)(H,22,26)(H,24,25)/t20-/m1/s1
• InChI Key: WDVALBSODAWGFX-HXUWFJFHSA-N
• Exact Mass: 368.13722174
• Molecular Formula: C20H20N2O5
• Molecular Weight: 368.4
• SMILES: C[C@@](CC(=O)N)(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Topological: 119
• Monoisotopic Mass: 368.13722174
• Synonyms: 1403590-50-0, (R)-N-Fmoc-alpha-methylasparagine, FMoc-alpha-Me-D-Asn-OH, D-Asparagine, N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-2-methyl-, (2R)-4-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methyl-4-oxobutanoic acid, (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-amino-2-methyl-4-oxobutanoic acid, MFCD28167051, DTXSID001182443, E85908, EN300-25482099, D-Asparagine,N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-2-methyl-, (2R)-3-carbamoyl-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2-methylpropanoic acid

Application

(R)-N-Fmoc-alpha-methylasparagine is widely used in peptide synthesis to introduce steric constraints and improve metabolic stability in therapeutic peptides. Its alpha-methylation prevents racemization during coupling steps, making it valuable for synthesizing enantiopure peptidomimetics. Researchers leverage this derivative in drug discovery for conditions like cancer and autoimmune diseases, where modified peptides enhance target binding. It is also employed in structural biology to study peptide-protein interactions with minimized conformational flexibility.

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