Site-Selective Esterifications of Polyol β-Hydroxyamides and Applications to Serine-Selective Glycopeptide Modifications
Site-Selective Esterifications of Polyol β-Hydroxyamides and Applications to Serine-Selective Glycopeptide Modifications
复制标题
多元醇 β-羟基酰胺的位点选择性酯化及其在丝氨酸选择性糖肽修饰中的应用
DOI：
10.1021/acs.orglett.9b02809
复制
发表时间：
2019
期刊：
影响因子：
5.2
通讯作者：
Hara Osamu
中科院分区：
文献类型：
--
作者：
Takemoto Kohei;Nishikawa Yasuhiro;Moriguchi Shohei;Hori Yuna;Kamezawa Yuki;Matsui Takami;Hara Osamu
研究了β-羟基酰胺在其它羟基存在下的选择性酰化反应。这种修饰成功的关键是使用吡啶酮肟酯作为酰化试剂与CuOTf组合的金属模板驱动的酰化。这种策略使得β-羟基基团能够在各种衍生物（包括空间位阻仲β-醇）中被位点选择性地酰化。这种方法的效用是展示了丝氨酸选择性修饰的糖肽与未保护的糖。
The site-selective acylations of β-hydroxyamides in the presence of other hydroxyl groups are described. Central to the success of this modification is the metal-template-driven acylation using pyridine ketoxime esters as acylating reagents in combination with CuOTf. This strategy enables β-hydroxyl groups to be site-selectively acylated in various derivatives, including sterically hindered secondary β-alcohol. The utility of this methodology is showcased by the serine-selective modification of a glycopeptide with unprotected sugar.