1242934-32-2 | (2S,4S)-Fmoc-4-trifluoromethyl-pyrrolidine-2-carboxylic acid

CAS:1242934-32-2 | (2S,4S)-Fmoc-4-trifluoromethyl-pyrrolidine-2-carboxylic acid,Description

The compound “(2S,4S)-Fmoc-4-trifluoromethyl-pyrrolidine-2-carboxylic acid” likely belongs to the class of organic compounds known as pyrrolidine carboxylic acids. These are compounds containing a pyrrolidine ring which bears a carboxylic acid group.

Synthesis Analysis

While specific synthesis methods for this compound are not available, similar compounds such as (2S,4S)-1-(tert-Butoxycarbonyl)-4-methoxypyrrolidine-2-carboxylic acid have been synthesized from commercially available starting materials with excellent diastereoselectivity.

Molecular Structure Analysis

The molecular structure of this compound is likely to be similar to that of other pyrrolidine carboxylic acids. It would contain a pyrrolidine ring, a carboxylic acid group, and a trifluoromethyl group.

Scientific Research Applications

• Application in 19F NMR

  • Field : Chemistry and Biochemistry.
  • Summary : (2S,4R)- and (2S,4S)-perfluoro-tert-butyl 4-hydroxyproline were synthesized (as Fmoc-, Boc-, and free amino acids) in 2−5 steps. These amino acids were incorporated in model α-helical and polyproline helix peptides.
  • Methods : The key step of each synthesis was a Mitsunobu reaction with perfluoro-tert-butanol, which incorporated a perfluoro-tert-butyl group, with nine chemically equivalent fluorines.
  • Results : Peptides containing these amino acids were sensitively detected by 19F NMR, suggesting their use in probes and medicinal chemistry.

• Application in Glioma Imaging

  • Field : Nuclear Medicine and Oncology.
  • Summary : The tracer (2S,4S)4– [18F]FPArg is expected to provide a powerful imaging method for the diagnosis and treatment of clinical tumors.
  • Methods : A simple synthetic method for the radiolabeled precursor of (2S,4S)4– [18F]FPArg in stable yield was obtained by adjusting the sequence of the synthetic steps.
  • Results : MicroPET–CT imaging of nude mice bearing orthotopic HS683–Luc showed that (2S,4S)4–[18F]FPArg can penetrate blood–brain barrier and image gliomas with a high contrast. Therefore, (2S,4S)4–[18F]FPArg is expected to be further applied in the diagnosis and efficacy evaluation of clinical glioma.
• Application in Amino Acid Synthesis
  • Field : Organic Chemistry.
  • Summary : A concise synthesis of (2R,4R)-4-hydroxyproline and (2S,4S)-4-hydroxyproline has been developed in enantiomerically pure form from commercially available starting materials with excellent diastereoselectivity.
  • Methods : The key step of the synthesis was a 5-exo-tet ring closure reaction, which is assumed to form a tightly bound chelation controlled transition state.
  • Results : This method provides a new approach to synthesize (2R,4R)-4-hydroxyproline and (2S,4S)-4-hydroxyproline, which are important building blocks in peptide synthesis.
• Application in Peptide Synthesis
  • Field : Biochemistry.
  • Summary : (2S,4R)- and (2S,4S)-perfluoro-tert-butyl 4-hydroxyproline were synthesized (as Fmoc-, Boc-, and free amino acids) in 2−5 steps. These amino acids were incorporated in model α-helical and polyproline helix peptides.
  • Methods : The key step of each synthesis was a Mitsunobu reaction with perfluoro-tert-butanol, which incorporated a perfluoro-tert-butyl group, with nine chemically equivalent fluorines.
  • Results : Peptides containing these amino acids were sensitively detected by 19F NMR, suggesting their use in probes and medicinal chemistry.

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