Effects of a Squalene Epoxidase Inhibitor, Terbinafine, on Ether Lipid Biosyntheses in a Thermoacidophilic Archaeon,
            <i>Thermoplasma acidophilum</i>

Kon, Takahide; Nemoto, Norio; Oshima, Tairo; Yamagishi, Akihiko

doi:10.1128/jb.184.5.1395-1401.2002

Cited by 24 publications

(35 citation statements)

References 30 publications

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“…A recent significant advance in tetraether lipid biosynthesis has been achieved in pulse-chase experiments using an inhibitor (terbinafine) of tetraether lipid formation (56,73) (Fig. 11).…”

Section: Inhibition Of Tetraether Lipid Synthesismentioning

confidence: 99%

Biosynthesis of Ether-Type Polar Lipids in Archaea and Evolutionary Considerations

Koga

Morii

2007

Microbiol Mol Biol Rev

305

263

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SUMMARY This review deals with the in vitro biosynthesis of the characteristics of polar lipids in archaea along with preceding in vivo studies. Isoprenoid chains are synthesized through the classical mevalonate pathway, as in eucarya, with minor modifications in some archaeal species. Most enzymes involved in the pathway have been identified enzymatically and/or genomically. Three of the relevant enzymes are found in enzyme families different from the known enzymes. The order of reactions in the phospholipid synthesis pathway (glycerophosphate backbone formation, linking of glycerophosphate with two radyl chains, activation by CDP, and attachment of common polar head groups) is analogous to that of bacteria. sn-Glycerol-1-phosphate dehydrogenase is responsible for the formation of the sn-glycerol-1-phosphate backbone of phospholipids in all archaea. After the formation of two ether bonds, CDP-archaeol acts as a common precursor of various archaeal phospholipid syntheses. Various phospholipid-synthesizing enzymes from archaea and bacteria belong to the same large CDP-alcohol phosphatidyltransferase family. In short, the first halves of the phospholipid synthesis pathways play a role in synthesis of the characteristic structures of archaeal and bacterial phospholipids, respectively. In the second halves of the pathways, the polar head group-attaching reactions and enzymes are homologous in both domains. These are regarded as revealing the hybrid nature of phospholipid biosynthesis. Precells proposed by Wächtershäuser are differentiated into archaea and bacteria by spontaneous segregation of enantiomeric phospholipid membranes (with sn-glycerol-1-phosphate and sn-glycerol-3-phosphate backbones) and the fusion and fission of precells. Considering the nature of the phospholipid synthesis pathways, we here propose that common phospholipid polar head groups were present in precells before the differentiation into archaea and bacteria.

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Section: Inhibition Of Tetraether Lipid Synthesismentioning

confidence: 99%

Biosynthesis of Ether-Type Polar Lipids in Archaea and Evolutionary Considerations

Koga

Morii

2007

Microbiol Mol Biol Rev

305

263

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“…Jung et al (23) suggested that the iso-diabolic acids would be biosynthesized by ,Ј coupling of two iso fatty acids. In Archaea, isoprenoid GDGTs are also thought to be produced from (partial) condensation of two glycerol diethers by ,Ј coupling of isoprenoid alkyl chains (27,28,36); note that the tail (where the condensation takes place) of the isoprenoid chain is identical to that of iso fatty acids. The proposed ,Ј coupling of two iso fatty acids to obtain iso-diabolic acids is in full agreement with the results obtained here: iso-C 15 fatty acid is the dominant iso fatty acid present, and the C 30 iso-diabolic acid is the only dicarboxylic acid present.…”

Section: Vol 77 2011mentioning

confidence: 99%

13,16-Dimethyl Octacosanedioic Acid ( iso -Diabolic Acid), a Common Membrane-Spanning Lipid of Acidobacteria Subdivisions 1 and 3

Damsté

Rijpstra

Hopmans

et al. 2011

Appl Environ Microbiol

386

205

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The distribution of membrane lipids of 17 different strains representing 13 species of subdivisions 1 and 3 of the phylum Acidobacteria, a highly diverse phylum of the Bacteria, were examined by hydrolysis and gas chromatography-mass spectrometry (MS) and by high-performance liquid chromatography-MS of intact polar lipids. Upon both acid and base hydrolyses of total cell material, the uncommon membrane-spanning lipid 13,16-dimethyl octacosanedioic acid (iso-diabolic acid) was released in substantial amounts (22 to 43% of the total fatty acids) from all of the acidobacteria studied. This lipid has previously been encountered only in thermophilic Thermoanaerobacter species but bears a structural resemblance to the alkyl chains of bacterial glycerol dialkyl glycerol tetraethers (GDGTs) that occur ubiquitously in peat and soil and are suspected to be produced by acidobacteria. As reported previously, most species also contained iso-C 15 and C 16:17C as major fatty acids but the presence of iso-diabolic acid was unnoticed in previous studies, most probably because the complex lipid that contained this moiety was not extractable from the cells; it could only be released by hydrolysis. Direct analysis of intact polar lipids in the Bligh-Dyer extract of three acidobacterial strains, indeed, did not reveal any membrane-spanning lipids containing iso-diabolic acid. In 3 of the 17 strains, ether-bound iso-diabolic acid was detected after hydrolysis of the cells, including one branched GDGT containing iso-diabolic acid-derived alkyl chains. Since the GDGT distribution in soils is much more complex, branched GDGTs in soil likely also originate from other (acido)bacteria capable of biosynthesizing these components.

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“…The second step that involves the production of (S)-2,3-di-O-geranylgeranylglyceryl phosphate (DGGGP) from GGGP and GGPP is catalyzed by a microsomal enzyme, DGGGP syn-thase (DGGGPS), although further information concerning this prenyltransferase has not been obtained at this time. DGGGP, which has been shown to be the intermediate of archaeal membrane lipids, as evidenced by an incorporation experiment by Eguchi et al (15), would be expected to subsequently undergo saturation of the alkyl group, modification of the polar head group, and the formation of the cyclic tetraether structure (16). However, comprehensive information concerning these biosynthetic reactions is not available: the genes and proteins involved and even the order of the reactions are unknown at this time, expect for some enzymes that catalyze the modification of polar head groups (17,18).…”

mentioning

confidence: 99%

(S)-2,3-Di-O-geranylgeranylglyceryl Phosphate Synthase from the Thermoacidophilic Archaeon Sulfolobus solfataricus

Hemmi

Shibuya

Takahashi

et al. 2004

Journal of Biological Chemistry

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The core structure of membrane lipids of archaea have some unique properties that permit archaea to be distinguished from the others, i.e. bacteria and eukaryotes. (S)-2,3-Di-O-geranylgeranylglyceryl phosphate synthase, which catalyzes the transfer of a geranylgeranyl group from geranylgeranyl diphosphate to (S)-3-O-geranylgeranylglyceryl phosphate, is involved in the biosynthesis of archaeal membrane lipids. Enzymes of the UbiA prenyltransferase family are known to catalyze the transfer of a prenyl group to various acceptors with hydrophobic ring structures in the biosynthesis of respiratory quinones, hemes, chlorophylls, vitamin E, and shikonin. The thermoacidophilic archaeon Sulfolobus solfataricus was found to encode three homologues of UbiA prenyltransferase in its genome. One of the homologues encoded by SSO0583 was expressed in Escherichia coli, purified, and characterized. Radio-assay and mass spectrometry analysis data indicated that the enzyme specifically catalyzes the biosynthesis of (S)-2,3-di-O-geranylgeranylglyceryl phosphate. The fact that the orthologues of the enzyme are encoded in almost all archaeal genomes clearly indicates the importance of their functions. A phylogenetic tree constructed using the amino acid sequences of some typical members of the UbiA prenyltransferase family and their homologues from S. solfataricus suggests that the two other S. solfataricus homologues, excluding the (S)-2,3-di-Ogeranylgeranylglyceryl phosphate synthase, are involved in the production of respiratory quinone and heme, respectively. We propose here that archaeal prenyltransferases involved in membrane lipid biosynthesis might be prototypes of the protein family and that archaea might have played an important role in the molecular evolution of prenyltransferases.The structures of membrane lipids have some interesting and remarkable properties that enable us to distinguish archaea from other organisms, i.e. eukaryotes and bacteria (1) (Fig. 1). Although the archaeal "diether" membrane lipids are homologues of glycerolipids in other organisms, they differ with respect to the following features: 1) The hydrocarbon moieties of the archaeal lipids are fully reduced C 20 or C 25 prenyl groups, whereas the ordinary glycerolipids contain linear acyl groups. 2) The alkyl groups are attached to glycerol via an ether bond in archaeal lipids, while glycerol and the acyl chains are ester-bonded in the bacterial and eukaryotic glycerolipids.3) The two groups of membrane lipids have opposite chiralities at their glycerol moieties; in short, the glycerol moieties of the archaeal and other glycerolipids are sn-2,3-di-O-alkylated and sn-1,2-di-O-acylated, respectively. Moreover, the existence of circular "tetraether" lipids, which are synthesized from two molecules of diether lipids in methanogenic and thermophilic archaea, emphasizes the uniqueness of the archaeal membrane lipids.The biosynthesis of the core structure of archaeal membrane lipids has been studied to date (Fig. 2). The genes of (all-E) geranylgeranyl diphos...

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Effects of a Squalene Epoxidase Inhibitor, Terbinafine, on Ether Lipid Biosyntheses in a Thermoacidophilic Archaeon, Thermoplasma acidophilum

Cited by 24 publications

References 30 publications

Biosynthesis of Ether-Type Polar Lipids in Archaea and Evolutionary Considerations

Biosynthesis of Ether-Type Polar Lipids in Archaea and Evolutionary Considerations

13,16-Dimethyl Octacosanedioic Acid ( iso -Diabolic Acid), a Common Membrane-Spanning Lipid of Acidobacteria Subdivisions 1 and 3

(S)-2,3-Di-O-geranylgeranylglyceryl Phosphate Synthase from the Thermoacidophilic Archaeon Sulfolobus solfataricus

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