Convergent Synthesis of N-Linked Glycopeptides via Aminolysis of ω-Asp p-Nitrophenyl Thioesters in Solution.
An efficient N-linked glycosylation reaction between glycosylamines and p-nitrophenyl thioester peptides has been developed. The reaction conditions are mild and compatible with the C-terminal free carboxylic acid group and the unprotected N-linked sialyloligosaccharide. By means of this convergent strategy, a versatile N-glycopeptide fragment containing an N-terminal Thz and a C-terminal thioester was readily prepared, which is available for the synthesis of long glycopeptides and glycoproteins using the protocol of native chemical ligation.
Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, CCNU-uOttawa Joint Research Centre, College of Chemistry, Central China Normal University , 152 Luoyu Road, Wuhan, Hubei 430079, P. R. China.
Jing-Jing
JJ
Du
Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, CCNU-uOttawa Joint Research Centre, College of Chemistry, Central China Normal University , 152 Luoyu Road, Wuhan, Hubei 430079, P. R. China.
Xiao-Fei
XF
Gao
Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, CCNU-uOttawa Joint Research Centre, College of Chemistry, Central China Normal University , 152 Luoyu Road, Wuhan, Hubei 430079, P. R. China.
Ling-Ming
LM
Xin
Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, CCNU-uOttawa Joint Research Centre, College of Chemistry, Central China Normal University , 152 Luoyu Road, Wuhan, Hubei 430079, P. R. China.
Ze
Z
Lei
Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, CCNU-uOttawa Joint Research Centre, College of Chemistry, Central China Normal University , 152 Luoyu Road, Wuhan, Hubei 430079, P. R. China.
Zheng
Z
Liu
Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, CCNU-uOttawa Joint Research Centre, College of Chemistry, Central China Normal University , 152 Luoyu Road, Wuhan, Hubei 430079, P. R. China.
Jun
J
Guo