N-Phenyl-N-aceto-vinylsulfonamides as Efficient and Chemoselective Handles for N-Terminal Modification of Peptides and Proteins

doi:10.1002/ejoc.201701715

	N-Phenyl-N-aceto-vinylsulfonamides as Efficient and Chemoselective Handles for N-Terminal Modification of Peptides and Proteins
	Huang, Rong 1,2,3; Li, Zhihong 2; Ren, Peiling 3; Chen, Wenzhang 2; Kuang, Yuanyuan 2; Chen, Jiakang 2; Zhan, Yuexiong 2; Chen, Hongli 2; Jiang, Biao 2
刊名	EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
	2018-02-14
期号	6 页码:829-836
关键词	Protein modifications N-terminal modification Regioselectivity Aza-Micheal addition Proteins
ISSN号	1434-193X
DOI	10.1002/ejoc.201701715
文献子类	Article
英文摘要	A number of vinylsulfonamides were synthesized and screened to identify reagents that can be used to modify octreotide under biological pH and room temperature with improved efficiency. N-Phenyl-N-aceto-vinylsulfonamide exhibits higher reactivity and has emerged as an efficient reagent that has the ability to realize the selective modification of peptides and proteins at the N-terminus via aza-Michael addition. We showed that, after conjugation of peptides and proteins with the reagent containing a bioorthogonal functional group, the derivatives could be further labelled by functionalities, including fluorescent tags, modified drugs and polyethylene glycol (PEG) polymers without the need for prior treatment. Somatostatin, lysozyme, and RNaseA were selectively modified at the N-terminus, which illustrated the application of the method.
资助项目	ShanghaiTech University[00000000]
WOS关键词	ALPHA-AMINO ; CROSS-LINKING ; NATIVE PEPTIDES ; FUNCTIONALIZATION ; BIOCONJUGATION ; LINKERS ; REAGENT ; DNA
WOS研究方向	Chemistry
语种	英语
出版者	WILEY-V C H VERLAG GMBH
WOS记录号	WOS:000425024900020
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/279902]
专题	中国科学院上海药物研究所
通讯作者	Chen, Hongli; Jiang, Biao
作者单位	1.Chinese Acad Sci, Shanghai Inst Mat Med, 555 Zu Chong Zhi Rd, Shanghai 201303, Peoples R China; 2.ShanghaiTech Univ, Shanghai Inst Adv Immunochem Studies, 99 Haike Rd, Shanghai 201210, Peoples R China; 3.Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China
推荐引用方式 GB/T 7714	Huang, Rong,Li, Zhihong,Ren, Peiling,et al. N-Phenyl-N-aceto-vinylsulfonamides as Efficient and Chemoselective Handles for N-Terminal Modification of Peptides and Proteins[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2018(6):829-836.
APA	Huang, Rong.,Li, Zhihong.,Ren, Peiling.,Chen, Wenzhang.,Kuang, Yuanyuan.,...&Jiang, Biao.(2018).N-Phenyl-N-aceto-vinylsulfonamides as Efficient and Chemoselective Handles for N-Terminal Modification of Peptides and Proteins.EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(6),829-836.
MLA	Huang, Rong,et al."N-Phenyl-N-aceto-vinylsulfonamides as Efficient and Chemoselective Handles for N-Terminal Modification of Peptides and Proteins".EUROPEAN JOURNAL OF ORGANIC CHEMISTRY .6(2018):829-836.