N-Linked Glycosyl Auxiliary-Mediated Native Chemical Ligation on Aspartic Acid: Application towards N-Glycopeptide Synthesis
Hua Chai
School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371 Singapore
These authors contributed equally to this work.
Search for more papers by this authorDr. Kim Le Mai Hoang
School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371 Singapore
These authors contributed equally to this work.
Search for more papers by this authorMinh Duy Vu
School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371 Singapore
Search for more papers by this authorDr. Kalyan Pasunooti
School of Biological Sciences, Nanyang Technological University, 60 Nanyang Drive, Singapore, 637551 Singapore
Search for more papers by this authorProf. Dr. Chuan-Fa Liu
School of Biological Sciences, Nanyang Technological University, 60 Nanyang Drive, Singapore, 637551 Singapore
Search for more papers by this authorCorresponding Author
Prof. Dr. Xue-Wei Liu
School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371 Singapore
Search for more papers by this authorHua Chai
School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371 Singapore
These authors contributed equally to this work.
Search for more papers by this authorDr. Kim Le Mai Hoang
School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371 Singapore
These authors contributed equally to this work.
Search for more papers by this authorMinh Duy Vu
School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371 Singapore
Search for more papers by this authorDr. Kalyan Pasunooti
School of Biological Sciences, Nanyang Technological University, 60 Nanyang Drive, Singapore, 637551 Singapore
Search for more papers by this authorProf. Dr. Chuan-Fa Liu
School of Biological Sciences, Nanyang Technological University, 60 Nanyang Drive, Singapore, 637551 Singapore
Search for more papers by this authorCorresponding Author
Prof. Dr. Xue-Wei Liu
School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371 Singapore
Search for more papers by this authorAbstract
A practical approach towards N-glycopeptide synthesis using an auxiliary-mediated dual native chemical ligation (NCL) has been developed. The first NCL connects an N-linked glycosyl auxiliary to the thioester side chain of an N-terminal aspartate oligopeptide. This intermediate undergoes a second NCL with a C-terminal thioester oligopeptide. Mild cleavage provides the desired N-glycopeptide.
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