Methods of synthesis of deuterium-labelled lipids

Thatacidic lipid was later shown to be a universal component of photosynthetictissues.

Hirsch J reported the reversed-phase separation of non polar lipids on a columnof polymerized vegetable oil (Factice) ().

Klenk E et al.

01/01/2018 · In the case of lipids, the synthesis of the ..

of the synthesisof oleic acid ().

Klenk E identified sphingomyelin as the stored phospholipid in cells frompatients with Niemann-Pick disease ().

Von Euler US identified a lipid-soluble substance from semen which stimulatesuterine smooth muscle contraction and named it prostaglandin ()


Upon adding phenol to deuterated water ..

T1 - Measurement of fractional lipid synthesis using deuterated water (2H2O) and mass isotopomer analysis

Fractional biosynthesis of palmitate, stearate, and cholesterol was determined with deuterated water (2H2O) using mass isotopomer analysis in Hep G2 and MCA sarcoma cells in culture. The method employed differs from previous ones in that the number of deuterium atoms from 2H2O incorporated into newly synthesized molecules was determined and not assumed. After correction for background natural abundances, the isotopomer distribution due to deuterium incorporation in fatty acids and cholesterol was shown to follow a simple binomial distribution depending on the deuterium enrichment in water (p) and the maximum number of deuterium atoms incorporated per molecule (N). Under a wide range of 2H2O enrichments, N could be determined to be 17 for palmitate, 20 for stearate, and 20 for cholesterol by regression analysis or from a series of consecutive mass isotopomer ratios. The fraction derived from de novo synthesis was given by the ratio of the observed to the theoretical deuterium enrichment, which is the product (N x p). The new synthesized fraction of palmitate and stearate by Hep G2 cells for the length of the experiment was found to be 77 and 65%, respectively. These values were confirmed by experiments with [U-13C]glucose as the precursor. In MCA sarcoma cells grown in lipid-poor medium, the average values for fractional synthesis of palmitate, stearate, and cholesterol were 70, 35, and 70%, respectively. This approach should be generally applicable to the simultaneous determination of fractional synthesis of a number of compounds with either deuterium or 13C tracers. Its application is only limited by the accuracy of mass spectrometric analysis.


Chemical deuteration by catalytic ..

AB - Phosphatidylcholine (PC) is a major component of eukaryotic cell membranes and one of the most commonly used phospholipids for reconstitution of membrane proteins into carrier systems such as lipid vesicles, micelles and nanodiscs. Selectively deuterated versions of this lipid have many applications, especially in structural studies using techniques such as NMR, neutron reflectivity and small-angle neutron scattering. Here we present a comprehensive study of selective deuteration of phosphatidylcholine through biosynthesis in a genetically modified strain of Escherichia coli. By carefully tuning the deuteration level in E. coli growth media and varying the deuteration of supplemented carbon sources, we show that it is possible to achieve a controlled deuteration for three distinct parts of the PC lipid molecule, namely the (a) lipid head group, (b) glycerol backbone and (c) fatty acyl tail. This biosynthetic approach paves the way for the synthesis of specifically deuterated, physiologically relevant phospholipid species which remain difficult to obtain through standard chemical synthesis.

Synthesis of deuterated 5(Z),11(Z)-eicosadienoic acid as …

In the framework of the platform, we will develop new synthesis procedures for deuterated monomers and polymers of topical interest that cannot be obtained via commercial suppliers, including isoprene, the basis of natural and synthetic rubbers, and polythiophenes, which are of high relevance for photovoltaic or applications. We will devise synthesis routes for thiophene-based labelled monomers. The technologies for the synthesis of the polymers are already established in our lab. In addition, we will synthesise polymer modification of lipids (ylated lipids) for biomedical applications and in the synthesis of biodegradable polymers based on polylactic acids, for which the enantiomerically pure L- and D- lactic acid monomers are synthesised.