Enzymatic synthesis of structured 1,2-diacyl-sn-glycero-3-phosphocholines from glycerol-sn-3-phosphocholine

• Main Authors: BLASI, FRANCESCA, COSSIGNANI, Lina, MAURIZI, Angela, SIMONETTI, Maria Stella, DAMIANI, Pietro
• Other Authors: Blasi, Francesca, Cossignani, Lina, Maurizi, Angela, Simonetti, Maria Stella, Damiani, Pietro
• Format: Article in Journal/Newspaper
• Language: English
• Published: 2008
• Subjects: sn-glycerol-3-phosphocholine; Novozym 435; Phospholipase A2; 1; 2-diacyl-sn-glycero-3-phosphocholine; Antarc*; Antarctica
• Online Access: http://hdl.handle.net/11391/158166

The synthesis of structured 1,2-diacyl-sn-glycero-3-phosphocholines (sn-1,2-PC) from glycerol-sn-3-phosphocholine (GPC) was studied by means of enzymatic acylation reactions of the two free sn- positions of the glycerol backbone. Already after 22 h high conversions (absolute yields = 100%) of GPC to sn-2-lysophosphatidylcholines (sn-2-LPC) were achieved using Novozym 435, a lipase from Candida antarctica, selective for the sn-1- position of GPC. In the second step the acylation of the sn-2- position of the sn-2-LPC was catalysed by phospholipase A2 from hog pancreas and better acylation yields (40% absolute yield, corresponding to a relative yield of 70%, when the reactions were carried out at controlled water activity) were obtained if compared to analogous reactions reported in the literature. A chemical procedure to obtain structured sn-1,2-PC from sn-2-LPC was also used and better results (65% absolute yield, corresponding to a relative yield of 95%) were obtained in comparison with the enzymatic method.