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CAS 198560-43-9

:

N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3,4-difluoro-L-phenylalanine

Description:
N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3,4-difluoro-L-phenylalanine, commonly referred to as Fmoc-3,4-difluoro-L-phenylalanine, is a derivative of the amino acid phenylalanine, modified to include a fluorenylmethoxycarbonyl (Fmoc) protecting group and two fluorine atoms at the 3 and 4 positions of the phenyl ring. This compound is characterized by its stability under basic conditions, making it useful in peptide synthesis, particularly in solid-phase peptide synthesis (SPPS). The presence of the Fmoc group allows for selective deprotection under mild conditions, facilitating the sequential addition of amino acids. The difluorination enhances the compound's hydrophobicity and can influence the conformational properties of peptides, potentially affecting their biological activity. Additionally, the compound is typically white to off-white in appearance and is soluble in organic solvents such as dimethyl sulfoxide (DMSO) and dimethylformamide (DMF). Its unique structural features make it a valuable building block in the design of fluorinated peptides and pharmaceuticals.
Formula:C24H19F2NO4
InChI:InChI=1S/C24H19F2NO4/c25-20-10-9-14(11-21(20)26)12-22(23(28)29)27-24(30)31-13-19-17-7-3-1-5-15(17)16-6-2-4-8-18(16)19/h1-11,19,22H,12-13H2,(H,27,30)(H,28,29)/t22-/m0/s1
InChI key:InChIKey=IHSYIDJNVXPQRM-QFIPXVFZSA-N
SMILES:C(OC(N[C@@H](CC1=CC(F)=C(F)C=C1)C(O)=O)=O)C2C=3C(C=4C2=CC=CC4)=CC=CC3
Synonyms:
  • <span class="text-smallcaps">L</span>-Phenylalanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-3,4-difluoro-
  • Fluorenylmethoxycarbonyl-L-3,4-Difluorophenylalanine
  • Fmoc-3,4-Difluoro-L-Phe-Oh
  • Fmoc-3,4-Difluoro-L-Phenylalanine
  • Fmoc-L-3,4-Difluorophenylalanine
  • Fmoc-L-Phe(3,4-F2)-Oh
  • Fmoc-Phe(3,4-DiF)-OH
  • Fmoc-Phe(3,4-F<sub>2</sub>)-OH
  • Fmoc-Phe(M,P-F2)-Oh
  • Fmoc-phe(3,4-f2)-oh
  • See more synonyms
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