Unit:
Κατεύθυνση Οργανική Σύνθεση και Εφαρμογές της στη Χημική ΒιομηχανίαLibrary of the School of Science
Author:
Bourmpoula Asimina
Supervisors info:
Κόκοτος Γεώργιος, Καθηγητής, Τμήμα Χημείας, Καποδιστριακό Πανεπιστήμιο Αθηνών
Mαγκριώτη Βικτωρία, Επίκουρη Καθηγήτρια, Τμήμα Χημείας, Καποδιστριακό Πανεπιστήμιο Αθηνών
Σταματία Βασιλείου, Επίκουρη Καθηγήτρια, Τμήμα Χημείας, Καποδιστριακό Πανεπιστήμιο Αθηνών
Original Title:
Σύνθεση 3-υδρόξυ και 4-υδρόξυ λιπαρών οξέων και δευτεριωμένων λιπαρών οξέων
Translated title:
Synthesis of 3-hydroxy and 4-hydroxy fatty acids and deuterated fatty acids
Summary:
Various polyunsaturated hydroxy fatty acids derived from polyunsaturated acid, such as hydroxy octadecadienoic acids, lipoxins, hydroxy eicosatetraenoic acids, hydroxy eicosapentaenoic acids, resolvins, protectins and maresins exhibit interesting biological activities. However, studies on the saturated hydroxy fatty acids are limited. 2-Hydroxy fatty acids are abundant in sphingolipids, while 3-hydroxy fatty acids are ubiquitously present as intermediates in the synthesis of fatty acids and β-oxidation and are building blocks of lipopolysaccharides. Recently, it has been reported that the GPR84 receptor is activated by medium chain fatty acids with a hydroxyl group at 2- or 3-positions most efficiently than the non-hydroxylated fatty acids.
Having therefore taken all of the above in mind, we developed a general method for the asymmetric synthesis of 3-hydroxy and 4-hydroxy fatty acids. Key-step for this synthesis was the organocatalytic asymmetric synthesis of terminal epoxides using third generation MacMillan’s catalyst.
Another class of compounds that has particularly attracted the interest is the fatty acid esters of hydroxy fatty acids, also known as FAHFAs. Thus, the synthesis of such an ester based on 4-hydroxy fatty acid was accomplished.
Finally, we have been interested in the synthesis of deuterated fatty acids containing, as they are of great utility in studies of biosynthesis and degradation pathways, but also in mass spectrometry studies as standard compounds.
Main subject category:
Science
Keywords:
3-Hydroxy fatty acids, ozonolysis, deuterated fatty acids, HRMS
Number of references:
145
