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Meeting key synthetic challenges in amanitin synthesis with a new cytotoxic analog: 5′-hydroxy-6′-deoxy-amanitin
Chemical Science ( IF 8.4 ) Pub Date : 2020-10-15 , DOI: 10.1039/d0sc04150e
Alla Pryyma 1 , Kaveh Matinkhoo 1 , Antonio A W L Wong 1 , David M Perrin 1
Affiliation  

Appreciating the need to access synthetic analogs of amanitin, here we report the synthesis of 5′-hydroxy-6′-deoxy-amanitin, a novel, rationally-designed bioactive analog and constitutional isomer of α-amanitin, that is anticipated to be used as a payload for antibody drug conjugates. In completing this synthesis, we meet the challenge of diastereoselective sulfoxidation by presenting two high-yielding and diastereoselective sulfoxidation approaches to afford the more toxic (R)-sulfoxide.

中文翻译:

使用新的细胞毒性类似物:5′-羟基-6′-脱氧-鹅膏蕈碱,应对鹅膏蕈碱合成中的关键合成挑战

认识到需要获得鹅膏蕈碱的合成类似物,在此我们报告了 5′-羟基-6′-脱氧鹅膏蕈碱的合成,这是一种新型的、合理设计的生物活性类似物和 α-鹅膏蕈碱的结构异构体,预计将被使用作为抗体药物缀合物的有效负载。在完成该合成过程中,我们通过提出两种高产率和非对映选择性磺化氧化方法来应对非对映选择性磺化氧化的挑战,以提供毒性更大的 ( R )-亚砜。
更新日期:2020-10-15
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