Regio- and Enantio-selective Chemo-enzymatic C−H-Lactonization of Decanoic Acid to (S)-δ-Decalactone
Jack Manning
Manchester Institute of Biotechnology (MIB), School of Chemistry, The University of Manchester, 131 Princess Street, M1 7DN Manchester, UK
Search for more papers by this authorDr. Michele Tavanti
Manchester Institute of Biotechnology (MIB), School of Chemistry, The University of Manchester, 131 Princess Street, M1 7DN Manchester, UK
Search for more papers by this authorDr. Joanne L. Porter
Manchester Institute of Biotechnology (MIB), School of Chemistry, The University of Manchester, 131 Princess Street, M1 7DN Manchester, UK
Search for more papers by this authorDr. Nico Kress
Manchester Institute of Biotechnology (MIB), School of Chemistry, The University of Manchester, 131 Princess Street, M1 7DN Manchester, UK
Search for more papers by this authorDr. Sam P. De Visser
School of Chemical Engineering and Analytical Science, The University of Manchester, Oxford Road, Manchester, M13 9PL UK
Search for more papers by this authorProf. Nicholas J. Turner
Manchester Institute of Biotechnology (MIB), School of Chemistry, The University of Manchester, 131 Princess Street, M1 7DN Manchester, UK
Search for more papers by this authorCorresponding Author
Prof. Sabine L. Flitsch
Manchester Institute of Biotechnology (MIB), School of Chemistry, The University of Manchester, 131 Princess Street, M1 7DN Manchester, UK
Search for more papers by this authorJack Manning
Manchester Institute of Biotechnology (MIB), School of Chemistry, The University of Manchester, 131 Princess Street, M1 7DN Manchester, UK
Search for more papers by this authorDr. Michele Tavanti
Manchester Institute of Biotechnology (MIB), School of Chemistry, The University of Manchester, 131 Princess Street, M1 7DN Manchester, UK
Search for more papers by this authorDr. Joanne L. Porter
Manchester Institute of Biotechnology (MIB), School of Chemistry, The University of Manchester, 131 Princess Street, M1 7DN Manchester, UK
Search for more papers by this authorDr. Nico Kress
Manchester Institute of Biotechnology (MIB), School of Chemistry, The University of Manchester, 131 Princess Street, M1 7DN Manchester, UK
Search for more papers by this authorDr. Sam P. De Visser
School of Chemical Engineering and Analytical Science, The University of Manchester, Oxford Road, Manchester, M13 9PL UK
Search for more papers by this authorProf. Nicholas J. Turner
Manchester Institute of Biotechnology (MIB), School of Chemistry, The University of Manchester, 131 Princess Street, M1 7DN Manchester, UK
Search for more papers by this authorCorresponding Author
Prof. Sabine L. Flitsch
Manchester Institute of Biotechnology (MIB), School of Chemistry, The University of Manchester, 131 Princess Street, M1 7DN Manchester, UK
Search for more papers by this authorAbstract
The conversion of saturated fatty acids to high value chiral hydroxy-acids and lactones poses a number of synthetic challenges: the activation of unreactive C−H bonds and the need for regio- and stereoselectivity. Here the first example of a wild-type cytochrome P450 monooxygenase (CYP116B46 from Tepidiphilus thermophilus) capable of enantio- and regioselective C5 hydroxylation of decanoic acid 1 to (S)-5-hydroxydecanoic acid 2 is reported. Subsequent lactonization yields (S)-δ-decalactone 3, a high value fragrance compound, with greater than 90 % ee. Docking studies provide a rationale for the high regio- and enantioselectivity of the reaction.
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