Inverse Electron-Demand Diels-Alder Bioconjugation Reactions Using 7-Oxanorbornenes as Dienophiles

被引：11
作者：
Agramunt, Jordi [1 ]
Ginesi, Rebecca [1 ]
Pedroso, Enrique [1 ,2 ]
Grandas, Anna [1 ,2 ]
机构：
[1] Univ Barcelona, Dept Quim Inorgan & Organ, Seccio Quim Organ, Barcelona 08028, Spain
[2] Univ Barcelona, Fac Quim, IBUB, Barcelona 08028, Spain
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 10期
关键词：
TETRAZINES; PEPTIDES;
D O I：
10.1021/acs.joc.0c00583
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Oligonucleotides, peptides, and peptide nucleic acids incorporating 7-oxanorbornene as a dienophile were reacted with tetrazines linked to either a peptide, D-biotin, BODIPY, or N-acetyl-D-galactosamine. The inverse electron-demand Diels-Alder (IEDDA) cycloaddition, which was performed overnight at 37 degrees C, in all cases furnished the target conjugate in good yields. IEDDA reactions with 7-oxanorbornenes produce a lower number of stereoisomers than that of IEDDA cycloadditions with other dienophiles.
引用
收藏
页码：6593 / 6604
页数：12
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