|
【结 构 式】 
|
【分子编号】43761 【品名】 【CA登记号】 |
【 分 子 式 】C160H267N35O50S3 【 分 子 量 】3577.28388 【元素组成】C 53.72% H 7.52% N 13.7% O 22.36% S 2.69% |
合成路线1
该中间体在本合成路线中的序号：(III)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.
| 【1】 White, H.S.; McCabe, R.T.; Armstrong, H.; et al.; 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. The Journal of Pharmacology and Experimental Therapeutics 2000, 292, 1, 425. |
| 【2】 McCabe, R.T.; Zhou, L.-M.; Layer, R.T. (Cognetix, Inc.); Use of conantokins. US 6172041; WO 9803189 . |
| 【3】 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); Conantokins. WO 9803541 . |