Description

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-methylbutanoic acid (CAS: 857478-30-9) is a high-purity, protected amino acid derivative widely used in peptide synthesis and pharmaceutical research. This compound features an Fmoc (9-fluorenylmethoxycarbonyl) protecting group, ensuring stability during solid-phase peptide synthesis (SPPS) while enabling selective deprotection under mild basic conditions. With a molecular formula of C₂₀H₂₁NO₄, it is a chiral, non-proteinogenic amino acid analog, ideal for introducing sterically hindered modifications into peptide chains. Its high solubility in organic solvents like DMF and dichloromethane makes it a versatile building block for medicinal chemistry and bioconjugation applications. Each batch is rigorously analyzed by HPLC, NMR, and mass spectrometry to guarantee ≥95% purity, meeting the stringent demands of research and industrial applications.

Properties

• CAS Number: 857478-30-9
• Complexity: 486
• IUPAC Name: (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methyl-butanoic acid
• InChI: InChI=1S/C20H21NO4/c1-3-20(2,18(22)23)21-19(24)25-12-17-15-10-6-4-8-13(15)14-9-5-7-11-16(14)17/h4-11,17H,3,12H2,1-2H3,(H,21,24)(H,22,23)/t20-/m0/s1
• InChI Key: DZSLHAJXIQCMLR-FQEVSTJZSA-N
• Exact Mass: 339.14705815
• Molecular Formula: C20H21NO4
• Molecular Weight: 339.4
• SMILES: CC[C@@](C)(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Topological: 75.6
• Monoisotopic Mass: 339.14705815
• Synonyms: 857478-30-9, Fmoc-IsoVal-OH, Fmoc-L-isovaline, (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-methylbutanoic acid, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-isovaline, (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methylbutanoic acid, MFCD12031688, Fmoc-a-Me-Gly(Ethyl)-OH, SCHEMBL6881610, DZSLHAJXIQCMLR-FQEVSTJZSA-N, AKOS024465032, DS-8338, FF72809, (S)-2-(Fmoc-amino)-2-methylbutanoic acid, DB-326900, CS-0084320, F12332, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-isovaline, (S)-N-alpha-(9-Fluorenylmethyloxycarbonyl)-alpha-ethylalanine

Application

This Fmoc-protected L-isovaline derivative is primarily used in peptide synthesis, particularly for incorporating sterically constrained residues into peptide backbones. It serves as a key intermediate in the development of peptidomimetics and bioactive compounds targeting enzyme inhibition or receptor modulation. Researchers also employ it in the synthesis of custom amino acid scaffolds for drug discovery and structural biology studies.

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