大麻素受体内源性配体2-花生四烯酸甘油酯的化学酶法合成
Chemoenzymatic Synthesis of 2-Arachidonoylglycerol, An Endogenous Ligand for Cannabinoid Receptors.
作者信息
Vadivel Subramanian K, Whitten Kyle M, Makriyannis A
机构信息
Center for Drug Discovery, 116 Mugar Hall, 360 Huntington Avenue, Northeastern University, Boston, MA 02115.
出版信息
Tetrahedron Lett. 2011 Mar 16;52(11):1149-1150. doi: 10.1016/j.tetlet.2011.01.047.
Abstract
A simple and efficient synthesis of 2-arachidonoyl glycerol, an endogenous agonist for cannabinoid receptors was achieved using Novozym 435, immobilized lipase from Candida Antarctica.
摘要
使用南极假丝酵母固定化脂肪酶诺维信435实现了大麻素受体内源性激动剂2-花生四烯酸甘油酯的简单高效合成。
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本文引用的文献
1
Highly efficient enzymatic synthesis of 2-monoacylglycerides and structured lipids and their production on a technical scale.2-单酰甘油和结构化脂质的高效酶促合成及其工业化生产
Lipids. 2007 Oct;42(10):947-53. doi: 10.1007/s11745-007-3084-y. Epub 2007 Jul 11.
2
Endocannabinoids and the regulation of their levels in health and disease.内源性大麻素及其在健康与疾病中的水平调节
Curr Opin Lipidol. 2007 Apr;18(2):129-40. doi: 10.1097/MOL.0b013e32803dbdec.
3
Biochemistry, pharmacology and physiology of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand.内源性大麻素受体配体2-花生四烯酸甘油酯的生物化学、药理学及生理学特性
Prog Lipid Res. 2006 Sep;45(5):405-46. doi: 10.1016/j.plipres.2006.03.003. Epub 2006 Apr 19.
4
The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications.内源性大麻素系统：药物靶点、先导化合物及潜在治疗应用。
J Med Chem. 2005 Aug 11;48(16):5059-87. doi: 10.1021/jm058183t.
5
Lipase-catalyzed synthesis of monoacylglycerol in a homogeneous system.脂肪酶在均相体系中催化合成单酰甘油。
Biotechnol Lett. 2003 Apr;25(8):641-4. doi: 10.1023/a:1023016215537.
6
Evidence that 2-arachidonoylglycerol but not N-palmitoylethanolamine or anandamide is the physiological ligand for the cannabinoid CB2 receptor. Comparison of the agonistic activities of various cannabinoid receptor ligands in HL-60 cells.有证据表明，2-花生四烯酸甘油酯而非N-棕榈酰乙醇胺或花生四烯酸乙醇胺是大麻素CB2受体的生理配体。比较不同大麻素受体配体在HL-60细胞中的激动活性。
J Biol Chem. 2000 Jan 7;275(1):605-12. doi: 10.1074/jbc.275.1.605.
7
Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compounds.
J Biol Chem. 1999 Jan 29;274(5):2794-801. doi: 10.1074/jbc.274.5.2794.
8
Anandamide amidohydrolase reacting with 2-arachidonoylglycerol, another cannabinoid receptor ligand.与另一种大麻素受体配体2-花生四烯酸甘油酯发生反应的花生四烯乙醇胺酰胺水解酶。
FEBS Lett. 1998 Jan 23;422(1):69-73. doi: 10.1016/s0014-5793(97)01603-7.
9
Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors.鉴定出一种存在于犬类肠道中、能与大麻素受体结合的内源性甘油单酯。
Biochem Pharmacol. 1995 Jun 29;50(1):83-90. doi: 10.1016/0006-2952(95)00109-d.
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