Amino acid bioconjugation via iClick reaction of an oxanorbornadiene-masked alkyne with a MnI(bpy)(CO)3-coordinated azide

被引：44

作者：

Henry, Lucas ^{[1
]}

Schneider, Christoph ^{[1
]}

Muetzel, Benedict ^{[1
]}

Simpson, Peter V. ^{[1
]}

Nagel, Christoph ^{[1
]}

Fucke, Katharina ^{[1
,2
]}

Schatzschneider, Ulrich ^{[1
]}

机构：

[1] Univ Wurzburg, Inst Anorgan Chem, D-97074 Wurzburg, Germany

[2] Univ Durham, Sch Med Pharm & Hlth, Stockton On Tees TS17 6BH, England

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 99期

关键词：

FREE TRIAZOLE FORMATION; CYCLOADDITION REACTIONS; 1,3-DIPOLAR CYCLOADDITION; CLICK CHEMISTRY; OXIME LIGATION; COMPLEXES; ACETYLIDE; LIGANDS;

D O I：

10.1039/c4cc07892f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The catalyst-free room temperature iClick reaction of an unsymmetrically 2,3-disubstituted oxanorbornadiene (OND) as a `` masked'' alkyne equivalent with [Mn(N-3)(bpy(CH3,CH3))(CO)(3)] leads to isolation of a phenylalanine ester bioconjugate, in which the model amino acid is linked to themetal moiety via a N-2-coordinated triazolate formed in a cycloaddition-retro-Diels-Alder (crDA) reaction sequence, in a novel approach to bioorthogonal coupling reactions based on metalcentered reactivity.

引用

页码：15692 / 15695

页数：4

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