A novel method to synthesize 1‐acyl‐sn‐glycero‐3‐phosphocholine and 1,2‐diacyl‐sn‐glycero‐3‐phosphocholine
作者： Balakrishna Marrapu , Lakshmi Karuna Mallampalli , Shiva Shanker Kaki , Badari Narayana Prasad Rachapudi
关键词:
摘要: A facile, efficient, solvent-free method for the synthesis of phosphocholines and lyso in excellent yields has been developed employing sn-glycero-3-phosphocholine-kieselguhr complex with shorter reaction times recycling kieselguhr further use. Fatty acids chain lengths C3–C6 C8–C18 formed 1,2-diacyl-sn-glycero-3-phosphocholines 1-acyl-sn-glycero-3-phosphocholines respectively. acid chlorides (C3–C18) resulted exclusively 1,2-diacyl-sn-glycero-3-phosphocholines. Practical applications: Synthetic methodology symmetrical phosphatidylcholines is described. The described uses as a catalyst reagent which can be recycled after reaction. By this gram quantities prepared without use any other acylating reagents. synthetic novel approach producing lysophosphatidylcholines have wide range applications. Synthesis 1-acyl-sn-glycero-3-phosphocholine 1,2-diacyl-sn-glycero-3-phosphocholine.
sci-hub.se 参考文章(42)
Stefano Servi, Phospholipases as Synthetic Catalysts Topics in Current Chemistry. ,vol. 200, pp. 127- 158 ,(1999) , 10.1007/3-540-68116-7_5
Ronald Eisler, Mercury hazards from gold mining to humans, plants, and animals. Reviews of Environmental Contamination and Toxicology. ,vol. 181, pp. 139- 198 ,(2004) , 10.1007/0-387-21733-9_4
Farzaneh S. Roodsari, Dongpei Wu, Gregory S. Pum, Joseph Hajdu, A New Approach to the Stereospecific Synthesis of Phospholipids. The Use of l-Glyceric Acid for the Preparation of Diacylglycerols, Phosphatidylcholines, and Related Derivatives Journal of Organic Chemistry. ,vol. 64, pp. 7727- 7737 ,(1999) , 10.1021/JO990414E
Patrick Adlercreutz, Ann-Marie Lyberg, Dietlind Adlercreutz, Enzymatic fatty acid exchange in glycero-phospholipids European Journal of Lipid Science and Technology. ,vol. 105, pp. 638- 645 ,(2003) , 10.1002/EJLT.200300832
Ken’ichi Ichihara, Hitomi Iwasaki, Kaori Ueda, Ryoko Takizawa, Hideko Naito, Mitsuhiro Tomosugi, Synthesis of phosphatidylcholine: an improved method without using the cadmium chloride complex of sn-glycero-3-phosphocholine Chemistry and Physics of Lipids. ,vol. 137, pp. 94- 99 ,(2005) , 10.1016/J.CHEMPHYSLIP.2005.06.001
Renato Rosseto, Niloufar Bibak, Rosemarie DeOcampo, Trishul Shah, Ara Gabrielian, Joseph Hajdu, A new synthesis of lysophosphatidylcholines and related derivatives. Use of p-toluenesulfonate for hydroxyl group protection. Journal of Organic Chemistry. ,vol. 72, pp. 1691- 1698 ,(2007) , 10.1021/JO062352F
Santanu Bhattacharya, Avinash Bajaj, Advances in gene delivery through molecular design of cationic lipids Chemical Communications. pp. 4632- 4656 ,(2009) , 10.1039/B900666B
Ezio Fasoli, Alberto Arnone, Antonio Caligiuri, Paola D'Arrigo, Lorenzo de Ferra, Stefano Servi, Tin-mediated synthesis of lyso-phospholipids Organic and Biomolecular Chemistry. ,vol. 4, pp. 2974- 2978 ,(2006) , 10.1039/B604636C
Carmen Virto, Patrick Adlercreutz, Lysophosphatidylcholine synthesis with Candida antarctica lipase B (Novozym 435) Enzyme and Microbial Technology. ,vol. 26, pp. 630- 635 ,(2000) , 10.1016/S0141-0229(00)00147-2
Andrew J. Lampkins, Edward J. O’Neil, Bradley D. Smith, Bio-orthogonal phosphatidylserine conjugates for delivery and imaging applications. Journal of Organic Chemistry. ,vol. 73, pp. 6053- 6058 ,(2008) , 10.1021/JO8011336