Peculiar membrane morphologies of archaebacterial lipid models: 1,1′-polymethylenebis(2-alkyl-sn-glycero-3-phosphocholine)

Yamauchi, Kiyoshi; Moriya, Atsushi; Kinoshita, Masayoshi

doi:10.1016/0005-2760(89)90249-x

Cited by 57 publications

(33 citation statements)

References 19 publications

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“…Yamauchi et al4 and also others have prepared an unbranched model compound with only one membrane‐spanning chain to avoid the challenge of macrocyclisation. When the C 32 chain had no methyl branches, however, the compound4 did not form closed liposomes, but flat extended sheets, and showed a high transition temperature ( T m ) of 61 °C, which is not observed for archaebacterial lipids. The insertion of isoprenoid phytanyl residues into C 16 chains led to a decrease in the value of T m and allowed the preparation of lipid vesicles 5.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Optically Pure Diglycerol Tetraether Model Lipids with Non‐Natural Branching Pattern

et al. 2011

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Three new, chain‐modified, optically pure diglycerol tetraether lipids with one membrane‐spanning chain have been synthesised. These lipids contain a different number and constitution of the methyl branches connected to the hydrophobic chains as compared with natural archaeal or other previously synthesised lipids. The correct chirality of the branched alkyl chain was introduced starting from commercially available (S)‐citronellyl bromide. For chain elongation the Cu‐catalysed Grignard coupling reaction was used. Suitable blocked glycerol ethers were condensed to the tetraether moieties by Grubbs metathesis. The insertion of two or four optically pure methyl branches at the 10‐ and/or 23‐positions of the alkyl chains are sufficient to mimic the main properties of natural tetraether lipids. In this context, it has been shown that these lipids can form closed lipid vesicles.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Optically Pure Diglycerol Tetraether Model Lipids with Non‐Natural Branching Pattern

et al. 2011

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“…This indicates that (PAR) 2 C 10 forms a multilayer at a higher surface pressure. Such a kind of multilayer was suggested to be formed by one monolayer slipping on the other and has already been observed in the literature 25…”

Section: Resultsmentioning

confidence: 59%

Controllable Growth of Straight Nanorods and Nanowires in the Langmuir Films of a Bolaamphiphilic PAR Derivative

et al. 2006

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A novel bolaamphiphilic compound, 1, 10-bis[3'-hydroxy-4'-(2''-pyridylazo)phenoloxy] decane [(PAR)2C10], was synthesized and its spreading film and in situ coordination with metal ions in the Langmuir monolayer at the air/water interface were investigated. It was found that (PAR)2C10 could be spread on the water surface, and the Langmuir film showed a phase transition from a flat conformation to a U-shaped conformation upon compression. Interfacial coordination between (PAR)2C10 and metal ions could occur in situ in the Langmuir monolayer. Depending on the concentration of the subphase, different coordination modes were observed. A 2:1 (ligand-PAR-to-metal-ion) complex was formed at a lower concentration of the subphase, while a 1:1 complex was obtained on the subphase with a higher concentration of the salt. Interestingly, very straight nanowires, extending to several micrometers, were observed in the AFM images of the films transferred from the subphase containing CuCl2 in higher concentrations. However, tortuous nanowires were observed under the subphase containing Cu(CH3COO)2. The formation of such kind of wire-like structures was only observed for the combination of the bolaamphiphilic PAR derivative with the Cu(II) ions. Other metal ions or the single-chain PAR derivative did not show this behavior. A possible growth mechanism of the nanowires was proposed based on the coordination of the bolaamphiphilic (PAR)2C10 with the Cu(II) ions as well as with the counteranions.

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“…Elferink et al [52] had reported 0.82 nm 2 for GDNT from S. acidocaldarius , which indicates upright orientation of the membrane spanning tetraether lipids, too. On the other hand, Yamauchi et al [53] had reported a molecular area of 0.9–1.4 nm 2 for synthetic tetraethers with one membrane-spanning chain and two shorter single chains. Horse-shoe orientation was considered at least for part of these molecules and was first theoretically postulated for MPL, too, especially from the computer model of a single MPL molecule with and without pentacycles [22].…”

Section: Model Membranesmentioning

confidence: 99%

The Main (Glyco) Phospholipid (MPL) of Thermoplasma acidophilum

Freisleben

2019

IJMS

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The main phospholipid (MPL) of Thermoplasma acidophilum DSM 1728 was isolated, purified and physico-chemically characterized by differential scanning calorimetry (DSC)/differential thermal analysis (DTA) for its thermotropic behavior, alone and in mixtures with other lipids, cholesterol, hydrophobic peptides and pore-forming ionophores. Model membranes from MPL were investigated; black lipid membrane, Langmuir-Blodgett monolayer, and liposomes. Laboratory results were compared to computer simulation. MPL forms stable and resistant liposomes with highly proton-impermeable membrane and mixes at certain degree with common bilayer-forming lipids. Monomeric bacteriorhodopsin and ATP synthase from Micrococcus luteus were co-reconstituted and light-driven ATP synthesis measured. This review reports about almost four decades of research on Thermoplasma membrane and its MPL as well as transfer of this research to Thermoplasma species recently isolated from Indonesian volcanoes.

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Peculiar membrane morphologies of archaebacterial lipid models: 1,1′-polymethylenebis(2-alkyl-sn-glycero-3-phosphocholine)

Cited by 57 publications

References 19 publications

Synthesis of Optically Pure Diglycerol Tetraether Model Lipids with Non‐Natural Branching Pattern

Synthesis of Optically Pure Diglycerol Tetraether Model Lipids with Non‐Natural Branching Pattern

Controllable Growth of Straight Nanorods and Nanowires in the Langmuir Films of a Bolaamphiphilic PAR Derivative

The Main (Glyco) Phospholipid (MPL) of Thermoplasma acidophilum

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