- Synthesis of symmetrical, single-chain, phenylene/biphenylenemodified bolaamphiphiles
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Two new, symmetrical, phenylene- or biphenylene- modified bolaamphiphiles bearing two phosphocholine headgroups and an alkyl spacer chain length of 32 and 36 carbon atoms, respectively, have been synthesised. The key step was the Cu(II)-catalysed Grignard reaction used either as a simultaneous bis-coupling procedure or in a stepwise homocoupling. Particularly with the use of the homo-coupling, we were able to separate the phenylene-free by-products from the desired products. This homo-coupling additionally offered the possibility of preparing unsymmetrical bolaamphiphiles. Conversion of the diols into bipolar phospholipids was achieved by bis-phosphorylation with β- bromoethylphosphoric acid dichloride and subsequent quarternisation with trimethylamine. Unlike previous studies with aliphatic bolaamphiphiles that formed flexible nanofibres in aqueous suspension, the bolaamphiphiles of the present study, containing phenylene- and biphenylene groups in the middle part of the alkyl spacer chain, formed small ellipsoidal aggregates at ambient temperature. Springer-Verlag 2012.
- Drescher, Simon,Sonnenberger, Stefan,Meister, Annette,Blume, Alfred,Dobner, Bodo
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- Synthesis of specific deuterated derivatives of the long chained stratum corneum lipids [EOS] and [EOP] and characterization using neutron scattering
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The synthesis of specific deuterated derivatives of the long chained ceramides [EOS] and [EOP] is described. The structural differences with respect to the natural compounds are founded in the substitution of the 2 double bonds containing linoleic acid by a palmitic acid branched with a methyl group in 10-position. The specific deuteration is introduced both in the branched and in the terminal methyl group, which was realized by common methods of successive deuteration of carboxylic groups in 3 steps. These modified fatty acids resp. the corresponding ceramides [EOS] and [EOP] were prepared for neutron scattering investigations. First results of these investigations were presented in this manuscript showing that the deuterated compounds could be detected in the stratum corneum lipid model membranes. The deuterated ceramides [EOS] and [EOP] are valuable tools to investigate the influence of these long chained ceramide species on the nanostructure of stratum corneum lipid model membranes.
- Sonnenberger, Stefan,Eichner, Adina,Schmitt, Thomas,Hau?, Thomas,Lange, Stefan,Langner, Andreas,Neubert, Reinhard H.H.,Dobner, Bodo
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p. 316 - 330
(2017/06/08)
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- General synthesis and aggregation behaviour of a series of single-chain 1,ω-Bis(phosphocholines)
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The synthesis and physicochemical characterisation of a series of polymethylene-1,ω-bis(phosphocholines) with even-numbered chain lengths between 22 and 32 carbon atoms is described. Two new synthetic strategies for the preparation of long-chain 1,ω-diols as hydrocarbon building blocks are presented. The temperature-dependent self-assembly of the single-chain bolaamphiphiles was investigated by cryo transmission electron microscopy (cryo-TEM), differential scanning calorimetry (DSC), and Fourier transform infrared spectroscopy (FTIR).
- Drescher, Simon,Meister, Annette,Blume, Alfred,Karlsson, Goeran,Almgren, Mats,Dobner, Bodo
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p. 5300 - 5307
(2008/02/11)
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- Synthesis of cosmetic ingredients
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A method of synthesis of ω-hydroxy fatty acid containing ceramides having the general structure (1). STR1 where A represents CH2 or --CH=CH--Y represents a residue of a C14 to C22 fatty acid having the structure (2) STR2 where Z is --OH or an epoxy oxygen x is an integer of from 12 to 20 y is an integer of from 20 to 40 z is 0 or an integer of from 1 to 4 a is an integer of from 8 to 50 b is an integer of from 10 to 100 and n is an integer of from 7 to 27.
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