ArticleBeilstein journal of organic chemistry2013
Synthesis of enantiomerically pure (2S,3S)-5,5,5-trifluoroisoleucine and (2R,3S)-5,5,5-trifluoro-allo-isoleucine.
Article in Beilstein journal of organic chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Tinker, Tailor, Soldier, Spy: The Diverse Roles That Fluorine Can Play within Amino Acid Side Chains.Molecules (Basel, Switzerland) · 2023Review
- Fluorinated Protein and Peptide Materials for Biomedical Applications.Pharmaceuticals (Basel, Switzerland) · 2022Review
- Fluorine-induced polarity increases inhibitory activity of BPTI towards chymotrypsin.RSC chemical biology · 2022Article
- Systematic Evaluation of Fluorination as Modification for Peptide-Based Fusion Inhibitors against HIV-1 Infection.Chembiochem : a European journal of chemical biology · 2021Article
- Article
- Hydrolysis, polarity, and conformational impact of C-terminal partially fluorinated ethyl esters in peptide models.Beilstein journal of organic chemistry · 2017Article
- Position-dependent impact of hexafluoroleucine and trifluoroisoleucine on protease digestion.Beilstein journal of organic chemistry · 2017Article
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Authors and funding
7 authors.
Funding
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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-allo-isoleucine (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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