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CAS 478183-71-0

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Fmoc-D-3-Nitrophenylalanine

Description:
Fmoc-D-3-Nitrophenylalanine is a derivative of the amino acid phenylalanine, characterized by the presence of a 3-nitro substituent on the aromatic ring and a fluorenylmethyloxycarbonyl (Fmoc) protective group on the amino group. This compound is typically used in peptide synthesis, particularly in solid-phase peptide synthesis (SPPS), where the Fmoc group serves as a temporary protecting group that can be easily removed under basic conditions. The nitro group introduces an electron-withdrawing effect, which can influence the reactivity and properties of the amino acid in peptide chains. Fmoc-D-3-Nitrophenylalanine is often utilized in the study of peptide interactions and in the development of bioactive compounds due to its unique structural features. Additionally, its solubility in organic solvents and stability under various conditions make it a valuable building block in synthetic chemistry. As with many chemical substances, proper handling and safety precautions are essential due to potential hazards associated with its use.
Formula:C24H20N2O6
InChI:InChI=1/C24H20N2O6/c27-23(28)22(13-15-6-5-7-16(12-15)26(30)31)25-24(29)32-14-21-19-10-3-1-8-17(19)18-9-2-4-11-20(18)21/h1-12,21-22H,13-14H2,(H,25,29)(H,27,28)/t22-/m1/s1
InChI key:InChIKey=UDIZJKKIJYRJIN-JOCHJYFZSA-N
SMILES:C(OC(N[C@H](CC1=CC(N(=O)=O)=CC=C1)C(O)=O)=O)C2C=3C(C=4C2=CC=CC4)=CC=CC3
Synonyms:
  • <span class="text-smallcaps">D</span>-Phenylalanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-3-nitro-
  • Fmoc-3-Nitro-D-phenylalanine
  • N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3-nitro-<span class="text-smallcaps">D</span>-phenylalanine
  • N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3-nitro-D-phenylalanine
  • 282: PN: US20070042401 PAGE: 38 claimed sequence
  • 989: PN: WO2006135786 PAGE: 71 claimed sequence
  • D-Phenylalanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-3-nitro-
  • 3-Nitro-D-phenylalanine, N-FMOC protected
  • FMOC-3-NITRO-L-PHENYLALANINE
  • Cbz-L-3-NO2-Phe-OH
  • See more synonyms
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