Enzymatic Baeyer-Villiger oxidation as the key step in decano-4-lactone and decano-5-lactone degradation by Sporobolomyces odorus.
The biosyntheses of aroma active gamma- and delta-lactones have been previously characterized in yeasts and plants by incubation of labeled fatty acid derivatives. The lactones were considered as end products. Liquid cultures of the lactone-producing yeast Sporobolomyces odorus were used to investigate catabolic pathways of the lactones by incubation of ethyl (+/-)-5-hydroxy(1-(13)C1)decanoate ((13C)-1b) and methyl (+/-)-4-hydroxy(1-(13)C1)decanoate ((13C)-7a). Aliquots of the culture broth were analyzed with GC/MS after CH2N2 derivatization. S. odorus degraded (13C)-1b to 5-oxo(1-(13)C1)decanoic acid ((13C)-2c) and, subsequently, to pentyl (1-(13)C1)pentanedioate ((13C)-3c) and 3-[(1-(13)C1)carboxypropyl] hexanoate ((13C)-4c) by a Baeyer-Villiger-type oxidation (BVO). In addition, the oxidation of (13C)-7a to 4-oxo(1-(13)C1)decanoic acid ((13C)-8c) and a BVO of (13C)-8c to hexyl (1-(13)C1)butanedioate ((13C)-9c) is reported. So far, BVO has been observed in bacteria and some fungi; the data presented indicate a BVO catalyzed by the yeast S. odorus in the course of endogenous lactone metabolism.
Garbe
Leif-A
LA
Technische Universität Berlin, Institut für Biotechnologie, Molekularanalytik, Seestrasse 13, D-13353 Berlin. Leif-A.Garbe@TU-Berlin.de
Tressl
Roland
R
D001487:Basidiomycota / Q000201:enzymology*; D003651:Decanoates / Q000737:chemistry / Q000378:metabolism*; D007783:Lactones / Q000737:chemistry / Q000378:metabolism*; D010084:Oxidation-Reduction
D003651:Decanoates; D007783:Lactones