Aerobic and anaerobic abiotic oxidation of squalene in the presence of hydroperoxides.

Abiotic oxidation of squalene in the presence of hydroperoxysterols was studied in seawater under aerobic and anaerobic conditions. This ubiquitous isoprenoid alkene is quickly degraded in the presence of oxygen and its oxidation results mainly in the production of tertiary alcohols and to a lesser extent of epoxides and secondary alcohols. Although the degradation of squalene logically slows down under anaerobic conditions, a significant oxidation affording similar products than in the case of aerobic degradation has been observed. These results show that hydroperoxysterols, which seem to be well preserved in Recent sediments, could contribute to the oxidation of unsaturated lipids (such as squalene) in sedimentary environments under oxic and anoxic conditions.

Visible light-dependent degradation of long-chain alkenes in killed cells of Emiliania huxleyi and Nannochloropsis salina.

Photosensitized degradation rates of phytoplanktonic n-alkenes under visible light exposure were determined in laboratory experiments. Killed cells of Emiliania huxleyi and Nannochloropsis salina were used as source of biogenic alkenes. In E. huxleyi killed cells, minor C31 and C33 n-alkenes were strongly photodegraded, while the major C37 and C38 n-alkenes appeared particularly recalcitrant towards photochemical processes. This particular photochemical recalcitrance has been attributed to the chemical structure and localization of these hydrocarbons in the cells. Most of the n-alkenes of N. salina were strongly photodegraded in killed cells. The photodegradation of phytoplanktonic alkenes showed apparent second-order kinetics with respect to light exposure, and the half-life doses obtained logically decrease with increasing number of double bonds in these compounds. These results strongly suggest that significant amounts of phytoplanktonic n-alkenes must be photodegraded in the euphotic zone of the oceans during senescence.

Synthesis of new N-substituted pyrrolidin-2-ones as cyclic analog of gamma-aminobutyric acid.

Some new N-substituted pyrrolidin-2-ones, cyclic analogs of baclofen and of 3-(5-methylbenzo[b]furan-2-yl)-gamma-aminobutyric acid, have been prepared starting from corresponding pyrrolidinones and characterized.

Isomers of substituted 3-benzo[b]furyl and 3-thienylaminobutyric acids as potent ligands of the GABA-B receptor: synthesis and preparative liquid chromatographic separation.

Baclofen (4-amino-3-(4-chlorophenyl)butyric acid) is the only selective agonist for GABA-B receptors. Its R-(-)-enantiomer is about 100 times more active than the S-(+)-enantiomer. In the search for new compounds that bind to GABA-B receptors, it is very important to clarify the structural requirements. The authors report the synthesis and separation of isomers of various 3-heteroaromatic (benzo[b]furan and thiophen) aminobutyric acids. The 4-amino-3-(7-methylbenzo[b]furan-2-yl)butanoic acid is a potent and specific ligand for GABA-B receptors, with an IC50 value of 5.4 microM for the displacement of [3H] GABA.