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L-buthionine-S-sulfoximine and L-buthionine-R-sulfoximine

机译:L-buthionine-S-sulfoximine和L-buthionine-R-sulfoximine

摘要

The pure isomers L-buthionine-S-sulfoximine and L-buthionine-R- sulfoximine are provided. The L-S-isomer has utility, for example, in causing the depletion of glutathione, a major protectant molecule in tumors and certain parasites. The L-R-isomer has utility as a compound decreasing further uptake and thus effect of the L-S-isomer and for causing glutathione depletion specific to the kidney. The isolation of pure isomers from L-buthionine-SR-sulfoximine enables treatment at lower dosages without cross effects.PPThe pure L-buthionine-S- sulfoximine isomer is obtained from L-buthionine-SR-sulfoximine by recrystallization preferably by forming a solution of L-buthionine-SR- sulfoximine in water at a concentration of 0.8M and cooling to form crystals enriched in the L-R-isomer and a filtrate enriched in L-S-isomer, drying the filtrate to obtain a solid, dissolving the solid in ethanol, adding trifluoroacetic acid to form acid salt and provide solvent, then adding hexane to cause crystal formation, then converting the crystals to the free zwitterion using ion exchange resin.PPBoth isomers can be separated concurrently by reverse phase chromatography in Cu.sup.++ /D-proline buffers.
机译:提供了纯的异构体L-丁硫氨酸-S-亚磺酰亚胺和L-丁硫氨酸-R-亚磺酰亚胺。 L-S-异构体可用于例如引起谷胱甘肽的消耗,谷胱甘肽是肿瘤和某些寄生虫中的主要保护分子。 L-R-异构体具有作为化合物的用途,该化合物降低了进一步的摄取,从而降低了L-S-异构体的作用,并引起了肾脏特有的谷胱甘肽耗竭。从L-丁硫氨酸-SR-亚砜亚胺中分离出纯的异构体使得能够以更低的剂量进行治疗而不会产生交叉效应。优选通过在水中以0.8M的浓度形成L-丁硫氨酸-SR-亚磺酰亚胺的溶液并冷却以形成富含LR-异构体的晶体和富含LS-异构体的滤液,将滤液干燥以获得固体,溶解将固体溶于乙醇中,加入三氟乙酸形成酸盐并提供溶剂,然后加入己烷导致晶体形成,然后使用离子交换树脂将晶体转化为游离的两性离子。在Cusup ++ / D-脯氨酸缓冲液中进行反相色谱

著录项

  • 公开/公告号US5171885A

    专利类型

  • 公开/公告日1992-12-15

    原文格式PDF

  • 申请/专利权人 CORNELL RESEARCH FOUNDATION INC.;

    申请/专利号US19910715898

  • 发明设计人 OWEN W. GRIFFITH;

    申请日1991-06-19

  • 分类号C07C53/128;

  • 国家 US

  • 入库时间 2022-08-22 04:59:02

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