- Synthesis of Two New Phospholipidic Fluorescent Probes for Membrane Studies.
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Two new fluorenyl-phospholipidic probes have been prepared in good yield by a Pd0/CuI-catalyzed cross-coupling reaction.
- Starck, Jean-Philippe,Nakatani, Yoichi,Ourisson, Guy
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- Synthesis of enantiopure ABC-type triacylglycerols
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The synthesis of twelve enantiopure structured triacylglycerols (TAGs) of the ABC type possessing three different fatty acids is described by a six-step chemoenzymatic approach starting from (S)-solketal. Eight of the TAGs possess two different saturated fatty acyl groups located in the sn-1 and sn-2 positions with an unsaturated fatty acyl group in the remaining sn-3 position of the glycerol skeleton, whereas the remaining four possess two different saturated acyl groups in the terminal sn-1 and sn-3 positions with an unsaturated acyl group in the sn-2 position. The former group was synthesised by a six-step chemoenzymatic route involving a highly regioselective immobilised Candida antarctica lipase. The second group was prepared by a similar six-step approach, that required two separate lipase steps. Such enantiopure TAGs are strongly demanded as standards for enantiospecific analysis of intact TAGs in fats and oils.
- Gudmundsson, Haraldur G.,Linderborg, Kaisa M.,Kallio, Heikki,Yang, Baoru,Haraldsson, Gudmundur G.
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- Synthesis and properties of photoactivatable phospholipid derivatives designed to probe the membrane-associate domains of proteins
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The total syntheses of photoactivatable phospholipidic probes 1 and 2 are described. These probes contain either an aryldiazonium function at their polar head (probes 1a and 1b) or an diazocyclohexadienonyl group attached to the end of one fatty acid side chain (probe 2) and have been designed to probe the lipid/water interface and the hydrophobic core of the membrane, respectively. The synthetic schemes include the possibility of incorporating a radio-labeled atom (tritium) for further labeling investigations. Both probes were stable in the dark under physiological conditions and could be efficiently photodecomposed at wavelengths above 300 nm, leading to the generation of highly reactive species, aryl cations and cyclohexadienonyl carbene, respectively. In addition, these probes displayed UV-absorption spectra which are compatible with tryptophan-mediated energy transfer photoactivation, which can lead potentially to an efficient mapping of the membrane-associate protein domains.
- Alcaraz, Marie-Lyne,Peng, Ling,Klotz, Philippe,Goeldner, Maurice
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p. 192 - 201
(2007/10/03)
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