Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides
Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides
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DOI：
10.1021/jo011148j
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发表时间：
2002-05-03
影响因子：
3.6
通讯作者：
Meldal, M
中科院分区：
文献类型：
--
作者：
Tornoe, CW;Christensen, C;Meldal, M
叠氮化物与炔烃的环加成是合成1H-[1,2,3]三唑的重要途径之一。本文报道了一种新的区域特异性铜(I)催化的1,3-偶极环加成到叠氮化物的固相反应。叔、仲、叔烷基叠氮化物、芳基叠氮化物和叠氮糖成功地用于铜催化的环加成反应，在肽主链或侧链上生成不同的1,4-取代[1,2,3]-三唑。该反应条件与在极性载体上合成固相多肽完全相容。铜(I)的催化作用温和而高效（在大多数情况下转化率为95%以上，纯度为95%），此外，2-叠氮-2-甲基丙酸的x射线结构已经得到了解决，得到了进入反应的1,3偶极子的结构信息。利用Mitsunobu反应制备了新型的保护fmoc的氨基叠氮化物。
The cycloaddition of azides to alkynes is one of the most important synthetic routes to 1H-[1,2,3]triazoles. Here a novel regiospecific copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes to azides on solid-phase is reported. Primary, secondary, and tertiary alkyl azides, aryl azides, and an azido sugar were used successfully in the copper(I)-catalyzed cycloaddition producing diversely 1,4-substituted [1,2,3]-triazoles in peptide backbones or side chains. The reaction conditions were fully compatible with solid-phase peptide synthesis on polar supports. The copper(I) catalysis is mild and efficient (> 95% conversion and purity in most cases) and furthermore, the X-ray structure of 2-azido-2-methylpropanoic acid has been solved, to yield structural information on the 1,3-dipoles entering the reaction. Novel Fmoc-protected amino azides derived from Fmoc-amino alcohols were prepared by the Mitsunobu reaction.