Optimized synthesis of phosphatidylserine.
The synthesis of phosphatidyl serine containing saturated fatty acids was thoroughly studied and optimized in order to establish a protocol amenable to large-scale synthesis. The key step was a one-pot multicomponent reaction involving an O-benzyl phosphorodiamidite, protected serine and diacylglycerol, followed by in situ oxidation of the resulting phosphite. In order to replace expensive and poorly stable tetrazole, a screening of substitutes was carried out and imidazolium chloride was selected as the best suited one.
Guanti
Giuseppe
G
Dipartimento di Chimica e Chimica Industriale, Università di Genova, via Dodecaneso 31, 16146, Genoa, Italy. guanti@chimica.unige.it
Banfi
L
L
Basso
A
A
Bondanza
L
L
Guglieri
G
G
Powles
K
K
Riva
R
R
D004075:Diglycerides / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry; D010718:Phosphatidylserines / Q000138:chemical synthesis*
D004075:Diglycerides; D007093:Imidazoles; D009943:Organophosphorus Compounds; D010718:Phosphatidylserines; C029899:imidazole