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CAS 177966-63-1

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fmoc-4-nitro-D-phenylalanine

Description:
Fmoc-4-nitro-D-phenylalanine is a derivative of the amino acid phenylalanine, characterized by the presence of a 4-nitro substituent on the aromatic ring and a fluorenylmethoxycarbonyl (Fmoc) protective group on the amino group. This compound is commonly used in peptide synthesis, particularly in solid-phase peptide synthesis (SPPS), due to the stability of the Fmoc group under basic conditions and its ease of removal under mild acidic conditions. The 4-nitro group introduces an electron-withdrawing effect, which can influence the reactivity and properties of the amino acid in peptide formation. Fmoc-4-nitro-D-phenylalanine is typically a white to off-white solid and is soluble in organic solvents such as dimethylformamide (DMF) and dimethyl sulfoxide (DMSO). Its unique structural features make it valuable in the development of peptides with specific functionalities, and it is often utilized in research and pharmaceutical applications. Safety data should be consulted, as with all chemical substances, to ensure proper handling and usage.
Formula:C24H20N2O6
InChI:InChI=1/C24H20N2O6/c27-23(28)22(13-15-9-11-16(12-10-15)26(30)31)25-24(29)32-14-21-19-7-3-1-5-17(19)18-6-2-4-8-20(18)21/h1-12,21-22H,13-14H2,(H,25,29)(H,27,28)/t22-/m0/s1
SMILES:c1ccc2c(c1)c1ccccc1C2COC(=N[C@@H](Cc1ccc(cc1)N(=O)=O)C(=O)O)O
Synonyms:
  • Fmoc-D-4-Nitrophenylalanine
  • FMOC-D-4-Nitrophe
  • Fmoc-D-Phe(4-NO2)-OH
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