Regio- and enantioselective oxidation of thiaoleic acids by an algal delta 12-desaturase.
In a non aerated incubation medium, the oxidation of the tested thiaoleic acids by C. vulgaris was regioselective. Moreover the non oxidised 14-thiaoleic acid had no influence on the endogenous fatty acid pattern whereas the 13-thiaoleic acid, readily oxidised by the microalgae, caused a significant 18:1 accumulation in phospholipids. Examination of the 13-thiaoleic acid metabolism revealed that up to 15% of the substrate was specifically oxidised in the phospholipids before being transferred into the neutral lipids class of C. vulgaris. Confirmation of the monooxygenase-like delta 12-desaturase intervention in this biotransformation was obtained by the stereochemical analysis of the optically active sulfoxide isolated from the endoplasmic phospholipids.
Fauconnot
L
L
Laboratoire de Chimie Organique et des Substances Naturelles, ESA CNRS 6052, Ecole Nationale Supérieure de Chimie de Rennes, France.
Nugier-Chauvin
C
C
Noiret
N
N
Poulain
S
S
Patin
H
H
D000214:Acyl Coenzyme A / Q000378:metabolism; D001711:Biotransformation; D002478:Cells, Cultured; D002708:Chlorella / Q000201:enzymology* / Q000378:metabolism; D050356:Lipid Metabolism; D009829:Oleic Acids / Q000378:metabolism*; D010084:Oxidation-Reduction; D010743:Phospholipids / Q000378:metabolism; D013230:Stearoyl-CoA Desaturase / Q000378:metabolism*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013454:Sulfoxides / Q000378:metabolism
D000214:Acyl Coenzyme A; D009829:Oleic Acids; D010743:Phospholipids; D013454:Sulfoxides; D013230:Stearoyl-CoA Desaturase