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CAS 205526-26-7

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N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-2-fluoro-L-phenylalanine

Description:
N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-2-fluoro-L-phenylalanine, commonly referred to as Fmoc-2-fluoro-L-phenylalanine, is a derivative of the amino acid phenylalanine, modified to include a fluorine atom at the 2-position of the phenyl ring. This compound features a fluorenylmethoxycarbonyl (Fmoc) protecting group, which is widely used in peptide synthesis to protect the amino group of amino acids during the formation of peptide bonds. The presence of the fluorine atom can influence the compound's electronic properties and steric hindrance, potentially affecting its reactivity and interactions in biological systems. Fmoc-2-fluoro-L-phenylalanine is typically utilized in the synthesis of peptides and proteins, particularly in the context of developing novel therapeutics or studying protein structure and function. Its stability under standard peptide coupling conditions and compatibility with various coupling reagents make it a valuable tool in organic and medicinal chemistry. Additionally, the compound's unique characteristics may contribute to the design of fluorinated peptides with enhanced biological activity or specificity.
Formula:C24H20FNO4
InChI:InChI=1S/C24H20FNO4/c25-21-12-6-1-7-15(21)13-22(23(27)28)26-24(29)30-14-20-18-10-4-2-8-16(18)17-9-3-5-11-19(17)20/h1-12,20,22H,13-14H2,(H,26,29)(H,27,28)/t22-/m0/s1
InChI key:InChIKey=ARHOAMSIDCQWEW-QFIPXVFZSA-N
SMILES:C(OC(N[C@@H](CC1=C(F)C=CC=C1)C(O)=O)=O)C2C=3C(C=4C2=CC=CC4)=CC=CC3
Synonyms:
  • (2S)-2-([[(9H-Fluoren-9-yl)methoxy]carbonyl]amino)-3-(2-fluorophenyl)propanoic acid
  • (2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(2-fluorophenyl)propanoate
  • <span class="text-smallcaps">L</span>-Phenylalanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-2-fluoro-
  • Fmoc-2-Fluoro-L-phenylalanine
  • Fmoc-L-2-Fluorophe
  • Fmoc-L-2-Fluorophenylalanine
  • Fmoc-Phe(2-F)-OH
  • L-2-Fluorophenylalanine, FMOC protected
  • N-(9-Fluorenylmethoxycarbonyl)-2-fluorophenyl-L-alanine
  • N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-2-fluoro-<span class="text-smallcaps">L</span>-phenylalanine
  • See more synonyms
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