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N ‐Phenyl‐ N ‐aceto‐vinylsulfonamides as Efficient and Chemoselective Handles for N‐Terminal Modification of Peptides and Proteins
Author(s) -
Huang Rong,
Li Zhihong,
Ren Peiling,
Chen Wenzhang,
Kuang Yuanyuan,
Chen Jiakang,
Zhan Yuexiong,
Chen Hongli,
Jiang Biao
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701715
Subject(s) - chemistry , bioorthogonal chemistry , reagent , pegylation , polyethylene glycol , combinatorial chemistry , peg ratio , bioconjugation , lysozyme , peptide , reactivity (psychology) , conjugate , biochemistry , click chemistry , organic chemistry , medicine , mathematical analysis , alternative medicine , mathematics , finance , pathology , economics
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.