GS-2888
Chemical Name: Nomega-(tert-Butoxycarbonyl)-L-arginyl-glycine ditetradecylamide dihydrochloride
CAS No. 175969-22-9
项目整合开发状态: Biological Testing
项目研究机构: Gilead (Originator), GlaxoSmithKline (Originator)
合成路线:Benzyloxycarbonylglycine (I) was coupled with N-hydroxysuccinimide in the presence of dicyclohexylcarbodiimide (DCC),and the resulting succinimidyl active ester (II) was condensed with dimiristylamine (III) to afford amide (IV).The benzyloxycarbonyl group was then removed by hydrogenolysis in the presence of palladium on carbon to yield amine (V).Coupling of this amine with Boc-protected L-arginine (VI) in the presence of diisopropylcarbodiimide (DIC) gave dipeptide (VII).Finally,partial deprotection of Boc groups with hydrochloric acid in dioxane provided the title compound.
📌 参考资料/链接：
参考文献标题:Cationic lipids for delivery of nucleic acids to cells
文献作者:Deprince,R.B.; Facchine,K.L.; Lewis,G.S.; Lewis,J.G.; Lin,K.-Y.; Matteucci,M.D.; Mook,R.A.Jr.; Wagner,R.W.(Gilead Sciences Inc.; Glaxo Wellcome plc)
参考来源:WO 9601841
📄 详细内容
合成路线:Benzyloxycarbonylglycine (I) was coupled with N-hydroxysuccinimide in the presence of dicyclohexylcarbodiimide (DCC),and the resulting succinimidyl active ester (II) was condensed with dimiristylamine (III) to afford amide (IV).The benzyloxycarbonyl group was then removed by hydrogenolysis in the presence of palladium on carbon to yield amine (V).Coupling of this amine with Boc-protected L-arginine (VI) in the presence of diisopropylcarbodiimide (DIC) gave dipeptide (VII).Finally,partial deprotection of Boc groups with hydrochloric acid in dioxane provided the title compound.
参考文献标题:A serum-resistant cytofectin for cellular delivery of antisense oligodeoxynucleotides and plasmid DNA
文献作者:Lewis,J.G.; et al.
参考来源:Proc Natl Acad Sci USA 1996,93(8),3177