Grubbs Metathesis

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Pierre Jacobs - One of the best experts on this subject based on the ideXlab platform.

Peter Quayle - One of the best experts on this subject based on the ideXlab platform.

Boris Van Berlo - One of the best experts on this subject based on the ideXlab platform.

Bodo Dobner - One of the best experts on this subject based on the ideXlab platform.

  • Structure–property relationships in a series of diglycerol tetraether model lipids and their lyotropic assemblies: the effect of branching topology and chirality
    Organic & biomolecular chemistry, 2014
    Co-Authors: Thomas Markowski, Simon Drescher, Annette Meister, Alfred Blume, Bodo Dobner
    Abstract:

    Three novel diglycerol tetraether lipids with one membrane-spanning chain have been synthesized. These lipids contain only two or four racemic methyl branches at selected positions of the hydrophobic chains in contrast to natural lipids from archaebacterial membranes with an isoprenoid substitution pattern. The insertion of the methyl moieties was realized starting from either (RS)-citronellyl bromide or the inexpensive methyl malonic acid ethyl ester. For chain elongation the Cu-catalysed Grignard coupling reaction was used. The preparation of diglycerol tetraethers was either performed by condensing suitable blocked monoglycerol diethers by Grubbs Metathesis or by reaction of the transmembrane C32-chain with blocked glycerols followed by further alkylation steps. Finally, we could show that the resulting lipids can form closed lipid vesicles comparable to the optically pure counterparts. Therefore, these much simpler lipids compared to the natural lipids from archaebacterial membranes are also suitable for preparation of stable tailored liposomes.

  • Synthesis of Optically Pure Diglycerol Tetraether Model Lipids with Non‐Natural Branching Pattern
    European Journal of Organic Chemistry, 2011
    Co-Authors: Thomas Markowski, Simon Drescher, Annette Meister, Gerd Hause, Alfred Blume, Bodo Dobner
    Abstract:

    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.

James Faulkner - One of the best experts on this subject based on the ideXlab platform.