Strategy for O-Alkylation of Serine and Threonine from Serinyl and Threoninyl Acetic Acids by Photoinduced Decarboxylative Radical Reactions: Connection between Serine/Threonine and Carbohydrates/Amino Acids at the Side Chain,The Journal of Organic Chemistry

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Strategy for O-Alkylation of Serine and Threonine from Serinyl and Threoninyl Acetic Acids by Photoinduced Decarboxylative Radical Reactions: Connection between Serine/Threonine and Carbohydrates/Amino Acids at the Side Chain
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2018-03-09 00:00:00 , DOI: 10.1021/acs.joc.8b00061
Takashi Yamamoto ₁ , Tomoya Iwasaki ₁ , Toshio Morita ₁ , Yasuharu Yoshimi ₁

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O-Alkylations of serine and threonine derivatives at the hydroxy group were achieved using photoinduced decarboxylative radical reactions of serinyl and threoninyl acetic acids with an organic photocatalyst without racemization under mild conditions. Photoinduced decarboxylative radical additions of serinyl and threoninyl acetic acids to electron-deficient alkenes provided linked serine and threonine with carbohydrates and amino acids at the side chain. In addition, O-methylations containing deuterium and O-benzylation of serine were performed under similar photochemical conditions.

中文翻译：

通过光诱导的脱羧自由基反应从丝氨酸和苏氨酸乙酸中的丝氨酸和苏氨酸进行O-烷基化的策略：丝氨酸/苏氨酸与碳水化合物/氨基酸在侧链上的连接

使用丝氨酸和苏氨酸乙酸与有机光催化剂的光诱导脱羧自由基反应在温和条件下不消旋地实现了丝氨酸和苏氨酸衍生物在羟基上的O-烷基化。将丝氨酸和苏氨酸乙酸光诱导脱羧自由基加成至缺电子的烯烃，可将丝氨酸和苏氨酸与侧链上的碳水化合物和氨基酸相连。另外，在相似的光化学条件下进行含有氘的O-甲基化和丝氨酸的O-苄基化。

更新日期：2018-03-09

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