Description

(S)-N-alpha-(9-Fluorenylmethyloxycarbonyl)-C-alpha-methyl-2,6-difluorophenylalanine (CAS No. 1223105-51-8) is a high-purity, synthetic amino acid derivative designed for advanced peptide synthesis and pharmaceutical research. This compound features an Fmoc-protected α-methyl-2,6-difluorophenylalanine backbone, making it ideal for solid-phase peptide synthesis (SPPS) and other applications requiring sterically hindered or fluorinated amino acids. With a molecular formula of C₂₅H₂₁F₂NO₄, it offers exceptional compatibility with standard coupling reagents and deprotection conditions. Its chiral (S)-configuration ensures enantioselective incorporation into peptide chains, while the 2,6-difluorophenyl group enhances metabolic stability and binding affinity in bioactive peptides. Packaged under inert conditions to guarantee stability, this product is rigorously tested by HPLC and NMR to meet the highest standards for research and industrial use.

Properties

• CAS Number: 1223105-51-8
• Complexity: 659
• IUPAC Name: (2S)-3-(2,6-difluorophenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methyl-propanoic acid
• InChI: InChI=1S/C25H21F2NO4/c1-25(23(29)30,13-19-21(26)11-6-12-22(19)27)28-24(31)32-14-20-17-9-4-2-7-15(17)16-8-3-5-10-18(16)20/h2-12,20H,13-14H2,1H3,(H,28,31)(H,29,30)/t25-/m0/s1
• InChI Key: MRIVYBRWULFPFJ-VWLOTQADSA-N
• Exact Mass: 437.14386448
• Molecular Formula: C25H21F2NO4
• Molecular Weight: 437.4
• SMILES: C[C@](CC1=C(C=CC=C1F)F)(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Topological: 75.6
• Monoisotopic Mass: 437.14386448
• Synonyms: 1223105-51-8, (S)-N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-C-ALPHA-METHYL-2,6-DIFLUOROPHENYLALANINE, 835-658-5, (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(2,6-difluorophenyl)-2-methylpropanoic acid, N-Fmoc-(S)-2,6-difluoro-|A-methylphenylalanine, (2S)-3-(2,6-difluorophenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methylpropanoic acid, L-Phenylalanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-2,6-difluoro-alpha-methyl-, L-Phenylalanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-2,6-difluoro-a-methyl-, Fmoc-alpha-Me-Phe(2,6-DiF)-OH, MFCD22989428, (S)-N-Fmoc-alpha-Methyl-2,6-difluorophenylalanine, Fmoc-a-Me-Phe(2,6-DiF)-OH, AKOS025290693, FF72833, AS-79538, DS-019130, CS-0439186, F12128, N-Fmoc-(S)-2,6-difluoro-beta-methylphenylalanine, (S)-N-Fmoc-alpha-Methyl-2,6-difluorophenylalanine (Fmoc-aMe-L-Phe(2,6-diF)-OH), L-Phenylalanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-2,6-difluoro-|A-methyl-, (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(2,6-difluorophenyl)-2-methylpropanoicacid

Application

This Fmoc-protected amino acid derivative is widely used in peptide synthesis for the development of fluorinated peptide therapeutics and protease inhibitors. Its sterically hindered structure is valuable for studying enzyme-substrate interactions and designing conformationally constrained peptides. Researchers also employ it in medicinal chemistry to enhance the metabolic stability and bioavailability of peptide-based drugs.

Safety and Hazards

GHS Hazard Statements

• H361 (100%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

Precautionary Statements

• P203, P280, P318, P405, and P501

Hazard Classes and Categories

• Repr. 2 (100%)

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