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CAS 205526-30-3

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N-[(9H-fluoren-9-ylmethoxy)carbonyl]-3,4,5-trifluoro-L-phenylalanine

Description:
N-[(9H-fluoren-9-ylmethoxy)carbonyl]-3,4,5-trifluoro-L-phenylalanine, commonly referred to as Fmoc-Trifluoro-L-phenylalanine, is a derivative of the amino acid phenylalanine, modified with a fluorenylmethoxycarbonyl (Fmoc) protecting group and trifluoromethyl substitutions. This compound is characterized by its stability under basic conditions, making it suitable for use in solid-phase peptide synthesis. The Fmoc group allows for easy removal under mild alkaline conditions, facilitating the sequential addition of amino acids during peptide assembly. The trifluoromethyl groups enhance the lipophilicity and potentially influence the electronic properties of the molecule, which can affect peptide folding and interactions. Additionally, the presence of the fluorenyl group contributes to the compound's photophysical properties, making it useful in various biochemical applications, including fluorescence studies. Overall, this compound is significant in peptide chemistry and bioconjugation due to its unique structural features and functional versatility.
Formula:C24H18F3NO4
InChI:InChI=1/C24H18F3NO4/c25-19-9-13(10-20(26)22(19)27)11-21(23(29)30)28-24(31)32-12-18-16-7-3-1-5-14(16)15-6-2-4-8-17(15)18/h1-10,18,21H,11-12H2,(H,28,31)(H,29,30)/t21-/m1/s1
SMILES:c1ccc2c(c1)c1ccccc1C2COC(=N[C@H](Cc1cc(c(c(c1)F)F)F)C(=O)O)O
Synonyms:
  • Fmoc-L-3,4,5-Trifluorophenylalanine
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