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CAS 169243-86-1

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(S)-N-FMOC-4-Fluorophenylalanine

Description:
(S)-N-FMOC-4-Fluorophenylalanine is a derivative of the amino acid phenylalanine, modified to include a 4-fluorophenyl group and a fluorenylmethyloxycarbonyl (FMOC) protecting group. This compound is characterized by its chiral nature, as indicated by the (S) configuration, which refers to the specific spatial arrangement of its atoms. The FMOC group serves as a protective moiety for the amino group, facilitating its use in peptide synthesis by preventing unwanted reactions during the coupling process. The presence of the fluorine atom in the 4-position of the phenyl ring can influence the compound's electronic properties and hydrophobicity, potentially affecting its interactions in biological systems. (S)-N-FMOC-4-Fluorophenylalanine is often utilized in the field of medicinal chemistry and peptide synthesis, particularly in the development of pharmaceuticals where precise amino acid configurations are crucial for biological activity. Its stability and reactivity make it a valuable intermediate in the synthesis of more complex peptide structures.
Formula:C24H19FNO4
InChI:InChI=1/C24H20FNO4/c25-16-11-9-15(10-12-16)13-22(23(27)28)26-24(29)30-14-21-19-7-3-1-5-17(19)18-6-2-4-8-20(18)21/h1-12,21-22H,13-14H2,(H,26,29)(H,27,28)/p-1/t22-/m0/s1
SMILES:c1ccc2c(c1)c1ccccc1C2COC(=N[C@@H](Cc1ccc(cc1)F)C(=O)[O-])O
Synonyms:
  • Fmoc-L-4-Fluorophenylalanine
  • Fmoc-4-Fluoro-L-Phe-OH
  • Fmoc-4-Fluoro-L-phenylalanine
  • Fmoc-L-4-Fluorophe
  • Fmoc-Phe(4-F)-OH
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