Heteronuclear NMR analysis of unsaturated fatty acids in poly(3-hydroxyalkanoates). Study of beta-oxidation in Pseudomonas putida.
Poly(3-hydroxyalkanoates) (PHAs) were isolated from Pseudomonas putida KT2442 cultivated on petroselenic acid, oleic acid, and linoleic acid to study beta-oxidation of unsaturated fatty acids. Both saturated and unsaturated medium chain length 3-hydroxy fatty acids were found to be constituents of these polymers. With the aid of proton-detected multiple quantum coherence and proton-detected multiple bond coherence NMR spectra the structures of the unsaturated monomers were identified as 3-hydroxy-5-cis-tetradecanoate for PHA produced on oleic acid, and 3-hydroxy-6-cis-dodecanoate and 3-hydroxy-5-cis-8-cis-tetradecadienoate for PHA produced on linoleic acid. The identified structures, which are derived from fatty acid degradation intermediates, indicate a degradation of oleic acid via the enoyl-CoA isomerase-dependent route and a degradation of linoleic acid via the dienoyl-CoA reductase-dependent route.
de Waard
P
P
Agrotechnological Research Institute, Wageningen, The Netherlands.
van der Wal
H
H
Huijberts
G N
GN
Eggink
G
G
D002247:Carbon Isotopes; D005230:Fatty Acids, Nonesterified / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D006859:Hydrogen; D006880:Hydroxy Acids / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D019787:Linoleic Acid; D008041:Linoleic Acids / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D019301:Oleic Acid; D009829:Oleic Acids / Q000378:metabolism; D010084:Oxidation-Reduction; D016958:Pseudomonas putida / Q000378:metabolism*
D002247:Carbon Isotopes; D005230:Fatty Acids, Nonesterified; D006880:Hydroxy Acids; D008041:Linoleic Acids; D009829:Oleic Acids; D019301:Oleic Acid; C008820:petroselinic acid; D006859:Hydrogen; D019787:Linoleic Acid