新产品编号:1770767
Chemical Name: N-[2-(3,4-Dimethoxyphenyl)ethyl]-3-[7-(1-ethylheptyl)-5-methyl-4-oxo-3,4-dihydroimidazo[5,1-f][1,2,4]triazin-2-yl]-N-methyl-4-propoxybenzenesulfonamide
项目整合开发状态: Biological Testing
项目研究机构: Bayer (Originator)
合成路线:The title peptide was originally isolated from the venom of the marine cone snail Conus radiatus in small quantities.The compound has also been obtained by solid-phase peptide synthesis starting from Fmoc-L-proline linked to p-alkoxybenzylalcohol resin (I).Removal of the Fmoc group was effected by treatment with tetrabutylammonium fluoride in DMF.Chain elongation was carried out by coupling with the respective Fmoc-protected amino acids using diisopropyl carbodiimide and 1-hydroxybenzotriazole in CH2Cl2-DMF,followed by deprotection cycles with tetrabutylammonium fluoride.Gamma-carboxy glutamic acid was incorporated as the protected bis-tert-butyl ester.The final protected peptide resin (III) was liberated and deprotected by using a mixture of trifluoroacetic acid,thioanisole,water,ethanedithiol and dichloromethane,and the resulting peptide was air oxidized at a pH of 7.8 to form the required disulfide bridge.
📌 参考资料/链接：
参考文献标题:Use of conantokins
文献作者:McCabe,R.T.; Zhou,L.-M.; Layer,R.T.(Cognetix,Inc.)
参考来源:US 6172041; WO 9803189
📄 详细内容
合成路线:The title peptide was originally isolated from the venom of the marine cone snail Conus radiatus in small quantities.The compound has also been obtained by solid-phase peptide synthesis starting from Fmoc-L-proline linked to p-alkoxybenzylalcohol resin (I).Removal of the Fmoc group was effected by treatment with tetrabutylammonium fluoride in DMF.Chain elongation was carried out by coupling with the respective Fmoc-protected amino acids using diisopropyl carbodiimide and 1-hydroxybenzotriazole in CH2Cl2-DMF,followed by deprotection cycles with tetrabutylammonium fluoride.Gamma-carboxy glutamic acid was incorporated as the protected bis-tert-butyl ester.The final protected peptide resin (III) was liberated and deprotected by using a mixture of trifluoroacetic acid,thioanisole,water,ethanedithiol and dichloromethane,and the resulting peptide was air oxidized at a pH of 7.8 to form the required disulfide bridge.
参考文献标题:Conantokins
文献作者:Shen,G.S.; Layer,R.T.; Colledge,C.; Abogadie,F.C.; Zhou,L.-M.; Cruz,L.J.; Rivier,J.E.; McCabe,R.T.; Hyllyard,D.R.; Jimenez,E.; Walker,C.; Olivera,B.M.(Cognetix,Inc.; University of Utah)
参考来源:WO 9803541
合成路线:The title peptide was originally isolated from the venom of the marine cone snail Conus radiatus in small quantities.The compound has also been obtained by solid-phase peptide synthesis starting from Fmoc-L-proline linked to p-alkoxybenzylalcohol resin (I).Removal of the Fmoc group was effected by treatment with tetrabutylammonium fluoride in DMF.Chain elongation was carried out by coupling with the respective Fmoc-protected amino acids using diisopropyl carbodiimide and 1-hydroxybenzotriazole in CH2Cl2-DMF,followed by deprotection cycles with tetrabutylammonium fluoride.Gamma-carboxy glutamic acid was incorporated as the protected bis-tert-butyl ester.The final protected peptide resin (III) was liberated and deprotected by using a mixture of trifluoroacetic acid,thioanisole,water,ethanedithiol and dichloromethane,and the resulting peptide was air oxidized at a pH of 7.8 to form the required disulfide bridge.
参考文献标题:In vitro and in vivo characterization of conantokin-R,a selective NMDA receptor antagonist isolated from the venom of the fish-hunting snail Conus radiatus
文献作者:White,H.S.; McCabe,R.T.; Armstrong,H.; Donevan,S.D.; Cruz,L.J.; Abogadie,F.C.; Torres,J.; Rivier,J.E.; Paarmann,I.; Hollmann,M.; Olivera,B.M.
参考来源:The Journal of Pharmacology and Experimental Therapeutics 2000,292(1),425