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

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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. © 2013 Erdbrink et al; licensee Beilstein-Institut.

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Erdbrink, H., Nyakatura, E. K., Huhmann, S., Gerling, U. I. M., Lentz, D., Koksch, B., & Czekelius, C. (2013). Synthesis of enantiomerically pure (2S,3S)-5,5,5-trifluoroisoleucine and (2R,3S)-5,5,5-trifluoro-allo-isoleucine. Beilstein Journal of Organic Chemistry, 9, 2009–2014. https://doi.org/10.3762/bjoc.9.236

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