Rearrangements and addition reactions of biarylazacyclooctynones and the implications to copper-free click chemistry

被引:24
作者
Chigrinova, Mariya [1 ,2 ]
McKay, Craig S. [1 ,2 ]
Beaulieu, Louis-Philippe B. [1 ,2 ]
Udachin, Konstantin A. [1 ]
Beauchemin, Andre M. [2 ]
Pezacki, John Paul [1 ,2 ]
机构
[1] Natl Res Council Canada, Ottawa, ON K1A 0R6, Canada
[2] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
PROMOTED 1,3-DIPOLAR CYCLOADDITIONS; AZIDE-ALKYNE CYCLOADDITION; LIVING CELLS; BIOORTHOGONAL REACTIONS; CYCLOOCTYNES; NITRONES; ANIMALS;
D O I
10.1039/c3ob40683k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Highly strained biarylazacyclooctynone (BARAC) and analogous bioconjugation reagents were shown to undergo novel rearrangement and addition reactions leading to tetracyclic products. This may limit their practical applicability as bioorthogonal reporters for imaging biomolecules within living systems.
引用
收藏
页码:3436 / 3441
页数:6
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