The lipids of archaebacteria

Rosa, Mario De; Gambacorta, Agata

doi:10.1016/0163-7827(88)90011-2

Cited by 450 publications

(339 citation statements)

References 66 publications

Supporting

Mentioning

329

Contrasting

Order By: Relevance

“…After solvent removal, 0.874 g of 1 (63% yield) was obtained as a light yellow oil. 1 3 Cl, 10 mg, 0.01 mmol). The mixture was stirred under 1 atm of H 2 at 25 °C overnight and filtered through a 0.5" pad of alumina, followed by a ~100 mL Et 2 O rinse.…”

Section: Synthesis Of C 32 Phytbasmentioning

confidence: 99%

Functional Reconstitution of the Integral Membrane Enzyme, Isoprenylcysteine Carboxyl Methyltransferase, in Synthetic Bolalipid Membrane Vesicles

et al. 2006

View full text Add to dashboard Cite

Three bipolar archaeal-type diglycerophosphocholine tetraether lipids (a.k.a., bolalipids) have been prepared to determine 1) the influence of molecular structure on the physical properties of bolalipid membranes and 2) their impact on the functional reconstitution of Ste14p, a membrane-associated isoprenylcysteine carboxyl methyltransferase from Saccharomyces cerevisiae. The three bolalipids synthesized were: C 20 BAS, C 32 BAS, and C 32 phytBAS. These bolalipid structures differ in that the C 20 BAS derivative has a short sn-1 glyceryl diether C 20 H 40 transmembrane alkyl chain and two ether-linked sn-2 n-decyl chains, whereas the C 32 BAS and C 32 phytBAS derivatives have a longer sn-1 diether C 32 H 64 membrane-spanning chain and two ether-linked sn-2 n-hexadecyl or phytanyl chains, respectively. Differential scanning calorimetry and temperature-dependent 31 P NMR was used to determine the gel-to-liquid crystalline phase transition temperatures of the bolalipids (C 32 BAS T m > 85 °C; C 32 phytBAS T m = 14 °C; C 20 BAS T m = 17°C). The bolalipid lateral diffusion coefficients, determined by fluorescence recovery after photobleaching at 20 °C, were 1.5 × 10 −8 and 1.8 × 10 −9 cm 2 /s for C 20 BAS and C 32 phytBAS, respectively. The mobility of C 32 BAS could not be measured at this temperature. Ste14p activity was monitored by an in vitro methyltransferase assay in reconstituted vesicle dispersions composed of DMPC, C 20 BAS:E. coli polar lipid, C 20 BAS:POPC, C 32 phytBAS:E. coli polar lipid, and C 32 phytBAS:POPC. Ste14p activity was lost in vesicles composed of 75-100 mol% C 20 BAS and 0-100 mol% C 32 BAS, but retained in vesicles with 0-50 mol% C 20 BAS and 0-100 mol% C 32 phytBAS. Confocal immunofluorescence microscopy confirmed the presence of Ste14p in 100 mol% C 20 BAS and 100 mol% C 32 phytBAS vesicle dispersions, even though the lamellar liquid crystalline phase thickness of C 20 BAS is only 32 Å. Since Ste14p activity was not affected by either the gel to liquid-crystal phase transition temperature of the lipid or the temperature of the assay, the low activity observed in 75-100 mol% C 20 BAS membranes can be attributed to hydrophobic mismatch between this bolalipid and the hydrophobic surface of Ste14p.Bolalipids, also called bolaamphiphiles, are a class of bipolar lipids found in the cell membranes of some Archaea. In many cases, these organisms can survive in extreme environments due to the presence of isoprenoid-based tetraether bolalipids in their membranes (1-5). The membrane-spanning bipolar structural motif confers increased stability to these membranes by effectively cross-linking the apposed leaflets of a bilayer membrane, thereby producing a monolayer membrane that functionally mimics a conventional membrane bilayer. † This work was supported by NIH CA112427, the NIH "Diversity in Biomedical Science Program" at Purdue University, and the Indiana 21 st Century Fund.Correspondence to: Christine A. Hrycyna; David H. Thompson. NIH Public Access Author ManuscriptBiochemistry. Author ...

show abstract

Section: Synthesis Of C 32 Phytbasmentioning

confidence: 99%

Functional Reconstitution of the Integral Membrane Enzyme, Isoprenylcysteine Carboxyl Methyltransferase, in Synthetic Bolalipid Membrane Vesicles

et al. 2006

View full text Add to dashboard Cite

show abstract

“…By contrast, mesophilic representatives of the crenarchaeota have recently been discovered and shown to be major contributors to the pelagic biomass (up to 20%) in the world's oceans [3]. Thus far, all identified members of the archaea have been found to contain glycerol diphytanyl diether and/or glycerol dibiphytanyl glycerol tetraether (GDGT) lipids in their cellular membranes [4]. The membrane lipids occur either as naked core lipids, or with phospho-and/or glyco-head groups that are introduced during biosynthesis [5].…”

mentioning

confidence: 99%

“…Despite the potentially large number of biphytanyl structures and combinations possible, only 9 GDGT structures of this type have been identified to date [4]. The expression and abundance of these lipids varies from species to species; the tetraether profiles of methanogenic archaea are often of low diversity and dominated by GDGT I, whereas thermophilic and hyperthermophilic archaea often exhibit a much greater array of GDGT lipids [4,8].…”

mentioning

confidence: 99%

“…A structural relative of Ia, often referred to as acyclic caldarchaeol (II, Figure 1), is also abundant in the cellular membranes of a significant proportion of the archaea [4]. This core lipid shares the same stereochemistry as Ia in both glycerol units and contains the same C 40 -biphytanyl linkage between the glycerol units.…”

mentioning

confidence: 99%

“…In particular, treatment of the methanolysis products with HI-LiAlH 4 yields the constituent biphytanyl hydrocarbons of tetraether lipids, which can be identified via gas chromatography-mass spectrometry (GC-MS) [18]. By comparing the mass spectral fragmentation of structures formed in these experiments with those afforded from reduction with deuterated reagents (i.e., LiAlD 4 replacing LiAlH 4 ), the position of any rings in the chain can be localized and the full structures of the biphytanyl chains determined [4].…”

mentioning

confidence: 99%

See 2 more Smart Citations

Rapid discrimination of archaeal tetraether lipid cores by liquid chromatography-tandem mass spectrometry

Knappy

Chong

Keely

2009

J. Am. Soc. Mass Spectrom.

View full text Add to dashboard Cite

Atmospheric pressure chemical ionization liquid chromatography-tandem mass spectrometry (APCI LC-MS/MS) of tetraether lipid cores of archaeal origin reveals distinct dissociation pathways for three classes of core lipid extracted from Methanobacter thermautotrophicus. Within these classes, two isobaric tetraether lipids, one a scarcely reported lipid constituent of M. thermautotrophicus and the other an artefact formed during extraction from cultured cells, were identified and distinguished via their MS 2 spectra. APCI LC-MS/MS discriminates different tetraether core lipid types and isobaric species and reveals the mass of the constituent biphytanyl chains within the tetraether cores, albeit without full elucidation of their structures. Furthermore, the method allows direct estimation of the relative proportions of tetraether core lipids from chromatographic peak area measurement, allowing rapid profiling of these compounds in microbiological and environmental extracts. (J Am Soc Mass Spectrom 2009, 20, 51-59)

show abstract

Analysis of intact tetraether lipids in archaeal cell material and sediments by high performance liquid chromatography/atmospheric pressure chemical ionization mass spectrometry

Hopmans

Schouten

Pancost

et al. 2000

Rapid Commun. Mass Spectrom.

456

146

View full text Add to dashboard Cite

A method combining normal phase high performance liquid chromatography (HPLC) with positive ion atmospheric pressure chemical ionization mass spectrometry (APCI-MS) was developed for the analysis of intact glycerol dialkyl glycerol tetraethers (GDGTs) in archaeal cell material and sediments. All GDGTs previously reported to occur in the thermophilic archaeon Sulfolobus solfataricus could be identified based on their mass spectra and retention time. Positive ion mass spectra consisted of abundant protonated molecules and fragment ions corresponding to loss of water and the glycerol moiety. In addition, two novel GDGTs representing alternative combinations of biphytanyl moieties were observed. Using this method, the tetraethers present in the thermophilic archaeon Metallosphaera sedula and two sediment samples were characterized. This rapid method will greatly contribute to the establishment of the sedimentary record of these compounds and increase our understanding of archaea and their occurrence in widely different environments.

show abstract

The lipids of archaebacteria

Cited by 450 publications

References 66 publications

Functional Reconstitution of the Integral Membrane Enzyme, Isoprenylcysteine Carboxyl Methyltransferase, in Synthetic Bolalipid Membrane Vesicles

Functional Reconstitution of the Integral Membrane Enzyme, Isoprenylcysteine Carboxyl Methyltransferase, in Synthetic Bolalipid Membrane Vesicles

Rapid discrimination of archaeal tetraether lipid cores by liquid chromatography-tandem mass spectrometry

Analysis of intact tetraether lipids in archaeal cell material and sediments by high performance liquid chromatography/atmospheric pressure chemical ionization mass spectrometry

Contact Info

Product

Resources

About