Vinyl sulfonamide synthesis for irreversible tethering <i>via</i> a novel α-selenoether protection strategy
作者:Gregory B. Craven、Dominic P. Affron、Philip N. Raymond、David J. Mann、Alan Armstrong
DOI:10.1039/c8md00566d
日期:——
sulfonamides are valuable electrophiles for targeted protein modification and inhibition. We describe a novel approach to the synthesis of terminal vinyl sulfonamides which uses mild oxidative conditions to induce elimination of an α-selenoether masking group. The method complements traditional synthetic approaches and typically yields vinyl sulfonamides in high purity after aqueous work-up without requiring
乙烯基磺酰胺是用于靶向蛋白质修饰和抑制的有价值的亲电试剂。我们描述了一种新型的合成末端乙烯基磺酰胺的新方法,该方法使用温和的氧化条件诱导消除α-硒醚掩蔽基团。该方法是对传统合成方法的补充,通常在进行水后处理后即可得到高纯度的乙烯基磺酰胺,而无需对最终的亲电子产品进行柱色谱分析。该方法学适用于不可逆蛋白质束缚中使用的共价片段的合成,并且可以使各种片段通过化学接头与乙烯基磺酰胺战斗部连接。使用胸苷酸合酶作为模型系统,乙二醇被鉴定为不可逆的蛋白质束缚的有效连接子。