Synthesis of enantiomerically pure (2S,3S)-5,5,5-trifluoroisoleucine and (2R,3S)-5,5,5-trifluoro-allo-isoleucine

Holger Erdbrink, Elisabeth K. Nyakatura, Susanne Huhmann, Ulla I.M. Gerling, Dieter Lentz, Beate Koksch, Constantin Czekelius

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

A practical route for the stereoselective synthesis of (2S,3S)-5,5,5- trifluoroisoleucine (L-5-F3Ile) and (2R,3S)-5,5,5-trifluoro-alloisoleucine (D-5-F3-allo-Ile) was developed. The hydrophobicity of L-5-F3Ile was examined and it was incorporated into a model peptide via solid phase peptide synthesis to determine its α-helix propensity. The α-helix propensity of 5-F3Ile is significantly lower than Ile, but surprisingly high when compared with 4'-F3Ile.

Original languageEnglish (US)
Pages (from-to)2009-2014
Number of pages6
JournalBeilstein Journal of Organic Chemistry
Volume9
DOIs
StatePublished - Oct 2 2013
Externally publishedYes

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Isoleucine
Peptides
Hydrophobicity

Keywords

  • Amino acids
  • CD-spectroscopy
  • Fluorine
  • Helix propensity
  • Organo-fluorine
  • Trifluoroisoleucine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of enantiomerically pure (2S,3S)-5,5,5-trifluoroisoleucine and (2R,3S)-5,5,5-trifluoro-allo-isoleucine. / Erdbrink, Holger; Nyakatura, Elisabeth K.; Huhmann, Susanne; Gerling, Ulla I.M.; Lentz, Dieter; Koksch, Beate; Czekelius, Constantin.

In: Beilstein Journal of Organic Chemistry, Vol. 9, 02.10.2013, p. 2009-2014.

Research output: Contribution to journalArticle

Erdbrink, Holger ; Nyakatura, Elisabeth K. ; Huhmann, Susanne ; Gerling, Ulla I.M. ; Lentz, Dieter ; Koksch, Beate ; Czekelius, Constantin. / Synthesis of enantiomerically pure (2S,3S)-5,5,5-trifluoroisoleucine and (2R,3S)-5,5,5-trifluoro-allo-isoleucine. In: Beilstein Journal of Organic Chemistry. 2013 ; Vol. 9. pp. 2009-2014.
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abstract = "A practical route for the stereoselective synthesis of (2S,3S)-5,5,5- trifluoroisoleucine (L-5-F3Ile) and (2R,3S)-5,5,5-trifluoro-alloisoleucine (D-5-F3-allo-Ile) was developed. The hydrophobicity of L-5-F3Ile was examined and it was incorporated into a model peptide via solid phase peptide synthesis to determine its α-helix propensity. The α-helix propensity of 5-F3Ile is significantly lower than Ile, but surprisingly high when compared with 4'-F3Ile.",
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AU - Nyakatura, Elisabeth K.

AU - Huhmann, Susanne

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AU - Lentz, Dieter

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