The role of cytochrome P450 monooxygenases in microbial fatty acid metabolism

Abstract

Cytochrome P450 monooxygenases (P450s) are a diverse collection of enzymes acting on various endogenous and xenobiotic molecules. Most of them catalyse hydroxylation reactions and one group of possible substrates are fatty acids and their related structures. In this minireview, the significance of P450s in microbial fatty acid conversion is described. Bacteria and yeasts possess various P450 systems involved in alkane and fatty acid degradation, and often several enzymes with different activities and specificities are retrieved in one organism. Furthermore, P450s take part in the formation of fatty acid-based secondary metabolites. Finally, there are a substantial number of microbial P450s displaying activity towards fatty acids, but to which no biological role could be assigned despite the often quite intense research.

The production of ω-hydroxy palmitic acid using fatty acid metabolism and cofactor optimization in Escherichia coli

“…In biotransformation, several strategies have been developed to introduce the hydroxyl group at specific positions in long carbon chains of FFA: (i) direct introduction of a hydroxyl group at specific sites using hydroxylase and P450 (Silke Schneider et al 1998;Matsunaga et al 1996); (ii) reduction to generate a double bond at specific sites and subsequent hydration in the double bond using desaturase and hydratase (Joo et al 2012), respectively; (iii) reduction to generate a double bond at specific sites and subsequent epoxidation, followed by hydrolysis using desaturase, epoxidase, and epoxide hydrolase (Jung et al 2012); and (iv) lipoxygenase and diol synthase in the presence of (cis,cis)-double bonds and a double bond generating dihydroxy form (Brash 1999;Jerneren and Oliw 2012), respectively. Among them, one of the most challenging steps studied till now is the control of the terminal position hydroxylation of long-chain FFA, called ω-hydroxylation (Van Bogaert et al 2011), since for other chemical catalysts and/or enzymes except P450s and non-heme di-iron monooxygenase (Schrewe et al 2014), it is difficult to carry out such reaction.…”

In vitro synthesis of 9,10-dihydroxyhexadecanoic acid using recombinant Escherichia coli

“…All these carry out mono-hydroxylation using different mechanisms of action. Cytochrome P450s catalyse the insertion of one oxygen atom from molecular oxygen into an organic substrate with NAD(P)H as a cofactor through electron transfer [2]. Hydratases produce 10-hydroxy fatty acids, wherein it uses water molecule to add a hydrogen atom and a hydroxyl group at C 9 and C 10 positions, respectively, on to the carbon–carbon cis -double bond of unsaturated fatty acids.…”

The MrCYP52 Cytochrome P450 Monoxygenase Gene of Metarhizium robertsii Is Important for Utilizing Insect Epicuticular Hydrocarbons

“…Thus, both plant and insect cuticles are covered by a waxy epicuticular layer comprising a mixture of long chain alkanes and related chemicals that represent the first barrier to environmental threats [1]. Most plant and insect diseases are caused by fungi that infect their hosts by direct penetration of the cuticle [2], but the fungal genes responsible for waxy layer degradation remain almost completely unexplored.…”