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Published on: September 21, 2021
Chemoenzymatic synthesis of (S)-hexafluoroleucine and (S)-tetrafluoroleucine
Hsien-Po Chiu1, Richard P Cheng
1Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, New York 14260-3000, USA.
Organic Letters
|November 30, 2007
Abstract:
We have developed a short chemoenzymatic synthesis for both (S)-5,5,5,5',5',5'-hexafluoroleucine (Hfl) and (S)-5,5,5',5'-tetrafluoroleucine (Qfl) on gram scale. Qfl was incorporated into a peptide using standard solid-phase peptide synthesis protocols to measure its helix propensity. The helix propensity for Qfl is 0.68 kcal.mol-1 more favorable compared to Hfl.

