Mechanism and effective factors of acyl migration of lysophospholipid

Abstract

The specificity hydrolysis Sn-1 fatty acyl of phospholipids by phospholipase A1 and the phenomenon of acyl migration in Sn-2-lysophosphatidylcholine (Sn-2-LPC) were demonstrated through 13C NMR, which provided fundamental basis for enzymatic reaction solution of phosphatidylcholine (PC) including Sn-1-lysophosphatidylcholine, Sn-2-LPC, and L-α-glycerylphosphorylcholine. Based on the automatic acyl migration mechanism of monoglycerides, the automatic acyl migration mechanism of Sn-2-LPC was speculated in the acid condition or alkali condition. The effects of reaction parameters on the acyl migration were then explored, including the polarity of the solution, pH, temperature, substrate concentration, and reaction time. The conditions of low acyl migration were as follows: isopropanol solvent, pH 7~8, temperature <35℃, defined substrate concentration, shorten reaction time. These results contributed to a data support for the synthesis of acyl mixture of phospholipids, detection of specific phospholipase A1, and the explanation of biosynthetic pathway (lysophospholipid intermediate) of the production mixed phospholipid.