非天然磷脂化合物磷脂酰基γ-羟基丁酸的合成

doi:10.16085/j.issn.1000-6613.2017-2409

化工进展 ›› 2018, Vol. 37 ›› Issue (10): 4029-4032.DOI: 10.16085/j.issn.1000-6613.2017-2409

非天然磷脂化合物磷脂酰基γ-羟基丁酸的合成

李环宇¹, 李冰麟¹, 王姣¹, 段丹丹¹, 张小里², 赵彬侠¹

1 西北大学化工学院, 陕西西安 710069;
2 西北大学食品科学与工程学院, 陕西西安 710069

收稿日期:2017-11-22 修回日期:2017-12-19 出版日期:2018-10-05 发布日期:2018-10-05
通讯作者: 张小里,教授,博士生导师,研究方向为生物催化过程。
作者简介:李环宇(1993-),女,硕士研究生,研究方向为生物催化过程。
基金资助:
陕西省重点研发计划项目（2018NY-131）。

Synthesis of a novel and non-natural phospholipid: phosphatidylbutyric acid

LI Huanyu¹, LI Binglin¹, WANG Jiao¹, DUAN Dandan¹, ZHANG Xiaoli², ZHAO Binxia¹

1 College of Chemical Engeering, Northwest University, Xi'an 710069, Shaanxi, China;
2 College of Food Science and Technology, Northwest University, Xi'an 710069, Shaanxi, China

Received:2017-11-22 Revised:2017-12-19 Online:2018-10-05 Published:2018-10-05

摘要/Abstract

摘要： 首次利用生物酶催化法对非天然磷脂化合物磷脂酰基γ-羟基丁酸（phosphatidylbutyric acid，PB）的合成工艺进行了系统的探究。采用磷脂酶D （phospholipase D，PLD）在有机溶媒-水两相体系中催化磷脂酰胆碱（phosphatidylcholine，PC）和γ-羟基丁酸钠（sodium γ-hydroxybutyrate）发生磷脂酰基转移反应合成PB。实验结果表明，有机溶媒、底物摩尔比、反应温度、水相pH都对磷脂酰基γ-羟基丁酸的制备有一定的影响。确定最佳工艺为：以氯仿为有机溶媒，底物摩尔比（γ-羟基丁酸钠/PC）为90：1，反应温度为30℃，水相pH为5.5，反应时间为6h，在此工艺条件下的磷脂酰基γ-羟基丁酸的产率为73.51%。

关键词: 磷脂酰基γ-羟基丁酸, γ-羟基丁酸钠, 磷脂酶D, 磷脂酰基转移

Abstract: The non-natural phosphatidylbutyric acid (PB) was synthesized for the first time using the enzyme-catalyzed method. It was synthesized by phospholipase D (PLD)-catalyzed transphosphatidylation of phosphatidylcholine (PC) with sodium γ-hydroxybutyrate in the liquid-liquid system. The operational conditions of transphosphatidylation were investigated systematically, including organic solvents, molar ratios of sodium γ-hydroxybutyrate to PC, temperature, pH, and the reaction time. The optimal reaction conditions were that:the best candidate of organic solvent was trichloromethane, the molar ratio of Sodium γ-Hydroxybutyrate to PC was 90:1, the reaction temperature was 30℃, pH was 5.5, and the reaction time was 6h. Under those optimal conditions, the highest yield of PB was 73.15%.

Key words: phosphatidylbutyric acid, sodium γ-hydroxybutyrate, phospholipase D, transphosphatidylation

中图分类号:

TQR971⁺.2

李环宇, 李冰麟, 王姣, 段丹丹, 张小里, 赵彬侠. 非天然磷脂化合物磷脂酰基γ-羟基丁酸的合成[J]. 化工进展, 2018, 37(10): 4029-4032.

LI Huanyu, LI Binglin, WANG Jiao, DUAN Dandan, ZHANG Xiaoli, ZHAO Binxia. Synthesis of a novel and non-natural phospholipid: phosphatidylbutyric acid[J]. Chemical Industry and Engineering Progress, 2018, 37(10): 4029-4032.

参考文献

[1] MAITRE M, KLEIN C, MENSAHNYAGAN A G. Mechanisms for the specific properties of γ-hydroxybutyrate in brain[J]. Medicinal Research Reviews, 2016, 36(3):363-388.
[2] CARTER L P, KOEK W, FRANCE C P. Behavioral analyses of GHB:receptor mechanisms[J]. Pharmacology & Therapeutics, 2009, 121(1):100.
[3] ANDRESEN H, AYDIN B E, MUELLER A, et al. An overview of gamma-hydroxybutyric acid:pharmacodynamics, pharmacokinetics, toxic effects, addiction, analytical methods, and interpretation of results[J]. Drug Testing & Analysis, 2011, 3(9):560.
[4] MEYER S, KLEINSCHMIDT S, GOTTSCHLING S, et al. Gamma-hydroxy butyric acid:neurotransmitter, sedative and party drug[J]. Wien. Med. Wochenschr., 2005, 155(13/14):315-322.
[5] MAO X, LIU Q, QIU Y, et al. Identification of a novel phospholipase D with high transphosphatidylation activity and its application in synthesis of phosphatidylserine and DHA-phosphatidylserine[J]. Journal of Biotechnology, 2017, 249:51.
[6] DAMNJANOVIC J, IWASAKI Y. Phospholipase D as a catalyst:application in phospholipid synthesis, molecular structure and protein engineering[J]. Journal of Bioscience & Bioengineering, 2013, 116(3):271-280.
[7] 姚娜, 张小里, 赵彬侠, 等. 磷脂酶D催化大豆磷脂合成磷脂酰丝氨酸工艺[J]. 化工进展, 2011, 30(s1):281-284. YAO N, ZHANG X L, ZHAO B X, et al. Research on the synthetic process of phosphatidylserine from soybean lecithin catalyzed by phospholipase D[J]. Chemical Industry and Engineering Progress, 2011, 30(s1):281-284.
[8] PRIETO M A, VAZQUEZ J A, MURADO M A. A new and general model to describe, characterize, quantify and classify the interactive effects of temperature and pH on the activity of enzymes[J]. Analyst, 2015, 140(10):3587-3602.
[9] CHAPPELL J S, MEYN A W, NGIM K K. The extraction and infrared identification of gamma-hydroxybutyric acid (GHB) from aqueous solutions[J]. Journal of Forensic Sciences, 2004, 49(1):52-59.

非天然磷脂化合物磷脂酰基γ-羟基丁酸的合成

Synthesis of a novel and non-natural phospholipid: phosphatidylbutyric acid

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 3

编辑推荐

Metrics

本文评价

[1]	邓杨敏, 李冰麟, 董文博, 杨开利, 张小里, 赵彬侠. 磷脂酰乙醇胺的酶促合成及底物抑制动力学[J]. 化工进展, 2017, 36(07): 2601-2606.
[2]	封娟娟, 朱南南, 邓杨敏, 韩晓玲, 张小里, 赵彬侠. 反复分批式反应提高磷脂酰丝氨酸的生产能力[J]. 化工进展, 2016, 35(04): 1180-1183.
[3]	刘媛媛，张小里，姚娜，李红亚，赵彬侠. 磷脂酶D的紫外诱变选育及发酵条件的优化[J]. 化工进展, 2012, 31(09): 2036-2038.