Chinese Journal of Organic Chemistry >
Mechanism and Effective Factors of Acyl Migration of Lysophospholipid
Received date: 2014-04-12
Revised date: 2014-07-14
Online published: 2014-08-26
Supported by
Project supported by the National Natural Science Foundation of China (No. 31301502), the Key Science and Technology Program of Henan Province (No. 132102110066) and the Special Foundation for Young Scientists of Henan Academy of Agricultural Sciences (No. 2013YQ25).
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.
Key words： lysophospholipid; acyl migration; mechanism; effective factors
Zhang Kangyi , Zhang Lixia , Qu Lingbo , Wang Xingguo , Liu Yuanfa . Mechanism and Effective Factors of Acyl Migration of Lysophospholipid[J]. Chinese Journal of Organic Chemistry, 2014 , 34(12) : 2529 -2536 . DOI: 10.6023/cjoc201404019
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