Unnatural Amino Acid Derivatives through Click Chemistry: Synthesis of Triazolylalanine Analogues.
Unnatural Amino Acid Derivatives through Click Chemistry: Synthesis of Triazolylalanine Analogues.
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通过点击化学非天然氨基酸衍生物：三唑基丙氨酸类似物的合成。
DOI：
10.1055/s-0036-1588510
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发表时间：
2017
期刊：
影响因子：
--
通讯作者：
Luzzio,FrederickA
中科院分区：
文献类型：
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作者：
Patil,PravinC;Luzzio,FrederickA
一种新的2-（1-氧代异吲哚啉-2-基）乙酸叔丁酯衍生物在六甲基二硅氮锂存在下用炔丙基溴选择性烷基化。除去叔丁基保护基后，所得的N-异吲哚啉基（乙炔基丙氨酸）衍生物在“点击条件”下与一系列叠氮化物反应。点击反应提供了一系列N-异吲哚啉基-1，2，3-三唑基丙氨酸衍生物作为游离羧酸。酯化后，N-异吲哚啉酮保护基通过在苄基位置的选择性氧化转化为更容易除去的邻苯二甲酰基。
A noveltert-butyl 2-(1-oxoisoindolin-2-yl)acetate derivative is selectively alkylated with propargyl bromide in the presence of lithium hexamethyldisilazide. After removal of thetert-butyl protecting group, the resultingN-isoindolinyl (ethynylalanine) derivative is reacted with a series of azides under ‘click conditions’. The click reactions afford an array ofN-isoindolinyl- 1,2,3-triazolylalanine derivatives as the free carboxylic acids. Following esterification, theN-isoindolinone protecting group is then transformed into the more easily removable phthaloyl group by selective oxidation at the benzylic position.