Site-Selective Modification of Secondary Amine Moieties on Native Peptides, Proteins, and Natural Products with Ynones

被引：0
|
作者：
Gao, Feng [1 ]
Chang, Mengyang [2 ]
Meng, Xiang [1 ]
Xu, Hang [1 ]
Gnawali, Giri [1 ]
Dong, Yue [1 ]
Lopez, Byrdie [2 ]
Wang, Wei [1 ,2 ,3 ]
机构：
[1] Univ Arizona, Dept Pharmacol & Toxicol, R Ken Coit Coll Pharm, Tucson, AZ 85721 USA
[2] Univ Arizona, Dept Chem & Biochem, Tucson, AZ 85721 USA
[3] Univ Arizona, Canc Ctr, Tucson, AZ 85719 USA
来源：
BIOCONJUGATE CHEMISTRY | 2023年 / 34卷 / 09期
关键词：
LYSINE METHYLATION; ARGININE METHYLATION;
D O I：
10.1021/acs.bioconjchem.3c00246
中图分类号：
Q5 [生物化学];
学科分类号：
071010 ; 081704 ;
摘要：
Site-selective modification of biologically relevant secondary amines in peptides, proteins, and natural products has been challenging due to the similar reactivity between primary and secondary amines. Even for the secondary amines, their reactivities are significantly influenced by their structures and environment. Herein, we report a ynone Michael bioconjugation method for selective modification of secondary amines in unprotected peptides and proteins and complex natural products. We show that fine tuning the electronic effect of the ynones enables controlling the Michael acceptor reactivity for the selective reaction with the structurally different secondary amines in densely functionalized complex structures and complicated biological environment.
引用
收藏
页码：1553 / 1562
页数：10
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