Chemoenzymatic synthesis of (S)-hexafluoroleucine and (S)-tetrafluoroleucine.
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.
Chiu
Hsien-Po
HP
Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, New York 14260-3000, USA.
Cheng
Richard P
RP
D002851:Chromatography, High Pressure Liquid; D005461:Fluorine / Q000737:chemistry*; D007930:Leucine / Q000138:chemical synthesis* / Q000737:chemistry
D005461:Fluorine; D007930:Leucine