Identification of phenyldecanoic acid as a constituent of triacylglycerols and wax ester produced by Rhodococcus opacus PD630

Alvarez, Héctor M.; Luftmann, Heinrich; Silva, Roxana A.; Cesari, Ana C; Viale, Alberto; Wältermann, Marc; Steinbüchel, Alexander

doi:10.1099/00221287-148-5-1407

Cited by 55 publications

(29 citation statements)

References 20 publications

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“…might be a hint for their importance as well as for a presumably complex relationship between the encoded gene products (74). The detection of phenyldecanoic acid as a constituent of WE (e.g., phenyldecyl-phenyldecanoate) and TAG in R. opacus PD630 grown with phenyldecane again demonstrated the ability of AtfA-like enzymes to utilize even bulky substrates (93).…”

Section: Other Atfa-like Acyltransferases In Different Bacteriamentioning

confidence: 95%

Acyltransferases in Bacteria

Röttig

Steinbüchel

2013

Microbiol Mol Biol Rev

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148

141

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SUMMARY Long-chain-length hydrophobic acyl residues play a vital role in a multitude of essential biological structures and processes. They build the inner hydrophobic layers of biological membranes, are converted to intracellular storage compounds, and are used to modify protein properties or function as membrane anchors, to name only a few functions. Acyl thioesters are transferred by acyltransferases or transacylases to a variety of different substrates or are polymerized to lipophilic storage compounds. Lipases represent another important enzyme class dealing with fatty acyl chains; however, they cannot be regarded as acyltransferases in the strict sense. This review provides a detailed survey of the wide spectrum of bacterial acyltransferases and compares different enzyme families in regard to their catalytic mechanisms. On the basis of their studied or assumed mechanisms, most of the acyl-transferring enzymes can be divided into two groups. The majority of enzymes discussed in this review employ a conserved acyltransferase motif with an invariant histidine residue, followed by an acidic amino acid residue, and their catalytic mechanism is characterized by a noncovalent transition state. In contrast to that, lipases rely on completely different mechanism which employs a catalytic triad and functions via the formation of covalent intermediates. This is, for example, similar to the mechanism which has been suggested for polyester synthases. Consequently, although the presented enzyme types neither share homology nor have a common three-dimensional structure, and although they deal with greatly varying molecule structures, this variety is not reflected in their mechanisms, all of which rely on a catalytically active histidine residue.

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Section: Other Atfa-like Acyltransferases In Different Bacteriamentioning

confidence: 95%

Acyltransferases in Bacteria

Röttig

Steinbüchel

2013

Microbiol Mol Biol Rev

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148

141

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“…Lipid bodies may also act as a deposit for toxic or useless fatty acids during growth on recalcitrant carbon sources, which have to be excluded from the plasma membrane and phospholipid (PL) biosynthesis (9,11). Furthermore, many TAG-accumulating bacteria are ubiquitous in soil, and in this habitat, water deficiency causing dehydration is a frequent environmental stress.…”

Section: Occurrence and Function Of Storage Lipids In Prokaryotesmentioning

confidence: 99%

“…Furthermore, TAG formation doesn't only depend on fatty acid de novo synthesis, as was revealed by growth experiments using alkanes and phenylalkanes as carbon sources. In this case, alkanes were directly oxidized and activated to the respective acyl-CoA thioesters and incorporated into TAGs (11).…”

Section: Structure and Properties Of Prokaryotic Lipid Inclusionsmentioning

confidence: 99%

Neutral Lipid Bodies in Prokaryotes: Recent Insights into Structure, Formation, and Relationship to Eukaryotic Lipid Depots

2005

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Many prokaryotes are able to accumulate large amounts of lipophilic compounds as inclusion bodies in the cytoplasm. Members of most genera synthesize polymeric lipids such as poly(3-hydroxybutyrate) (PHB) or other polyhydroxyalkanoates (PHAs) (125), whereas accumulation of triacylglycerols (TAGs) and wax esters (WEs) in intracellular lipid-bodies is a property of only a few prokaryotes (10). Like the formation of PHAs, TAG and WE biosynthesis is also promoted in response to stress imposed on the cells and during imbalanced growth, for example by nitrogen limitation, if an abundant carbon source is present at the same time. All these lipids act as storage compounds for energy and carbon needed for maintenance of metabolism and synthesis of cellular metabolites during starvation and in particular if growth resumes. Although neutral lipid metabolism in bacteria, especially WE biosynthesis, has attracted increasing biotechnological interest, there has so far been little interest in medical research in the formation of prokaryotic lipid bodies. However, recent findings suggest that lipid body formation and accumulation of TAGs play an important role in the metabolism of the pathogenic bacteria like Mycobacterium tuberculosis (37,52).In contrast to the restricted occurrence of storage TAGs in prokaryotes, intracellular TAGs are widespread in many eukaryotes (34,35,40,53,65,106,112,132,133). In eukaryotes, storage lipids are also deposited as lipid bodies. Their structure and formation have recently been reviewed in detail by several authors, but additional information on prokaryotic lipid-bodies has been only superficial (98,100,151). In contrast, intracellular accumulation of WEs as a storage lipid is a great exception in eukaryotes and occurs only in jojoba (Simmondsia chinensis) (147), and PHAs are not at all synthesized as a storage compound in eukaryotes.The number of studies investigating the enzymatic and structural fundamentals of storage lipid metabolism in bacteria has increased drastically in the last years, providing the knowledge that storage lipids in bacteria have a similar important metabolic function like in eukaryotes. This review will focus on prokaryotic neutral lipid bodies in comparison with the currently discussed models for lipid body structure and their formation in eukaryotes and with PHA inclusions in prokaryotes.

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“…These species were quantified by measuring the abundance of protonated fatty acid product ions obtained by collisional activation for the [M1H] 1 ions using multiple reaction monitoring (MRM) experiments (12). Only one study has been published concerning the use of electrospray ionization (ESI) to characterize wax esters, perhaps because of the apparent insensitivity of this technique for neutral lipids (13). In that study, ESI was used to define the molecular weight of an aromatic wax ester isolated from Rhodococcus bacteria by measuring its sodium adduct [M1Na] 1 ion.…”

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confidence: 99%

Electrospray mass spectrometry of human hair wax esters

Fitzgerald

Murphy

2007

Journal of Lipid Research

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Wax esters extracted from human hair have been examined by capillary GC-MS and by nano electrospray ionization (ESI) mass spectrometry using a tandem quadrupole mass spectrometer. Initially, the wax esters were examined by capillary GC-MS using conventional means, thus revealing an incomplete chromatographic resolution of the complex array of .200 wax esters ranging from 28 to 40 carbons in length, including saturated/straight-chained, unsaturated/straight-chained, saturated/branched, and unsaturated/branched molecular species. ESI of wax esters produced ammonium adduct ions [M1NH 4 ] 1 , and collisional activation of these ions formed abundant [RCO 2 H 2 ] 1 product ions. Wax esters containing a double bond in the fatty acyl or fatty alcohol portion of the molecule revealed identical behavior, suggesting little influence of the double bond on the ionization process or subsequent decomposition. The wax ester mixture was analyzed by ESI and tandem mass spectrometry using multiple reaction monitoring and neutral loss scanning. The neutral loss experiment [loss of NH 3 and CH 2 5CH-(CH 2 ) n CH 3 ] was particularly effective at rapidly surveying the complex biological mixture, identifying .160 different wax esters that range from 24 to 42 total carbons.-Fitzgerald, M., and R.C. Murphy. Electrospray mass spectrometry of human hair wax esters. J. Lipid

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Identification of phenyldecanoic acid as a constituent of triacylglycerols and wax ester produced by Rhodococcus opacus PD630

Cited by 55 publications

References 20 publications

Acyltransferases in Bacteria

Acyltransferases in Bacteria

Neutral Lipid Bodies in Prokaryotes: Recent Insights into Structure, Formation, and Relationship to Eukaryotic Lipid Depots

Electrospray mass spectrometry of human hair wax esters

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