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CS-W001157 4
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N-Fmoc-(S)-2,6-difluoro-α-methylphenylalanine

  • CAS No. 1223105-51-8

  • Cat. No. CS-0439186
  • Purity≥97%
  • MDL No.MFCD22989428

*For research and further manufacturing use only, not for direct human use.

N-Fmoc-(S)-2,6-difluoro-α-methylphenylalanine|CS-0439186

Structure of 1223105-51-8

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General Information

  • CAS No. 1223105-51-8
  • Cat. No. CS-0439186
  • Purity ≥97%
  • MDL No. MFCD22989428
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₅H₂₁F₂NO₄
  • Molecular Weight 437.44
  • Synonym(s) (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(2,6-difluorophenyl)-2-methylpropanoic acid
  • SMILES FC(C=CC=C1F)=C1C[C@](C(O)=O)(C)NC(OCC2C3=CC=CC=C3C4=CC=CC=C42)=O

Description

N-Fmoc-(S)-2,6-difluoro-α-methylphenylalanine is a sterically hindered, electron-deficient amino acid derivative designed for peptide synthesis. The α-methyl group confers conformational rigidity, while the ortho-fluorine substituents enhance metabolic stability and modulate electronic properties. This residue integrates seamlessly into challenging sequences, offering improved solubility and resistance to enzymatic degradation under standard coupling conditions.

Application

N-Fmoc-(S)-2,6-difluoro-α-methylphenylalanine serves as a valuable building block for the synthesis of bioactive peptides and peptidomimetics. The ortho-difluoro substitution enhances metabolic stability and modulates electronic properties, while the α-methyl group confers conformational rigidity and resistance to proteolytic degradation. The Fmoc protecting group enables efficient solid-phase peptide synthesis with straightforward deprotection under mild basic conditions. This derivative facilitates the incorporation of sterically constrained, electron-deficient aromatic side chains into target scaffolds with high reliability and reproducibility.

Safety Information

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GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   75.63
  • LogP   4.8893
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   6

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