Open AccessChemoenzymatic Synthesis of (S)-Hexafluoroleucine and (S)-Tetrafluoroleucine
Author(s) -
HsienPo Chiu,
Richard P. Cheng
Publication year - 2007
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/ol702470j
Subject(s) - helix (gastropod) , computer science , scale (ratio) , peptide , chemistry , physics , biochemistry , ecology , quantum mechanics , snail , biology
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.
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