Description

FMoc-alpha-Me-D-Phe(2-F)-OH (CAS No. 1315449-93-4) is a high-purity, fluorinated phenylalanine derivative designed for advanced peptide synthesis and pharmaceutical research. This compound features an Fmoc (9-fluorenylmethoxycarbonyl) protecting group, ensuring compatibility with solid-phase peptide synthesis (SPPS) protocols. Its molecular formula, C₂₅H₂₂FNO₄, and stereospecific (R)-configuration make it ideal for constructing modified peptides with enhanced stability, bioavailability, or targeted activity. The 2-fluorophenyl and alpha-methyl modifications introduce steric and electronic effects, valuable for structure-activity relationship (SAR) studies. Packaged under inert conditions to guarantee stability, this reagent is rigorously tested by HPLC and NMR to meet the stringent demands of medicinal chemistry and bioconjugation applications.

Properties

• CAS Number: 1315449-93-4
• Complexity: 635
• IUPAC Name: (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(2-fluorophenyl)-2-methyl-propanoic acid
• InChI: InChI=1S/C25H22FNO4/c1-25(23(28)29,14-16-8-2-7-13-22(16)26)27-24(30)31-15-21-19-11-5-3-9-17(19)18-10-4-6-12-20(18)21/h2-13,21H,14-15H2,1H3,(H,27,30)(H,28,29)/t25-/m1/s1
• InChI Key: VNYGHKCAXQKZEQ-RUZDIDTESA-N
• Exact Mass: 419.15328635
• Molecular Formula: C25H22FNO4
• Molecular Weight: 419.4
• SMILES: C[C@@](CC1=CC=CC=C1F)(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Topological: 75.6
• Monoisotopic Mass: 419.15328635
• Synonyms: 1315449-93-4, FMoc-alpha-Me-D-Phe(2-F)-OH, (R)-N-Fmoc-alpha-methyl-2-fluorophenylalaine, (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(2-fluorophenyl)-2-methylpropanoic acid, Fmoc-alpha-methyl-D-2-Fluorophe, 193086-74-7, (R)-N-alpha-(9-Fluorenylmethyloxycarbonyl)-C-alpha-methyl-2-fluorophenylalanine, (r)-n-fmoc-alpha-methyl-2-fluorophenylalanine, Fmoc-alpha-methyl-L-2-Fluorophe, Fmoc-|A-methyl-D-2-Fluorophe, MFCD17019320, Fmoc-|A-Me-D-Phe(2-F)-OH, AKOS030212537, AS-59266, CS-0439225, F90326, S-1315449-93-4, Fmoc-alpha-methyl-L-2-fluorophenylalanine (Fmoc-L-aMePhe(2-F)-OH), D-Phenylalanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-2-fluoro-|A-methyl-, (2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(2-fluorophenyl)-2-methylpropanoic acid

Application

FMoc-alpha-Me-D-Phe(2-F)-OH is primarily used in peptide synthesis to incorporate fluorinated, non-natural amino acids into peptide chains, enabling modulation of peptide conformation and metabolic stability. It serves as a key building block in drug discovery for probing fluorination effects on receptor binding or enzymatic resistance. Researchers also employ it in the development of peptide-based therapeutics, diagnostics, and biomaterials where fluorine’s unique properties are leveraged.

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