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High-Yielding Staudinger Ligation of a Phosphinothioester and Azide To Form a Peptide

Bradley L. Nilsson, Laura L. Kiessling and Ronald T. Raines

*Departments of Chemistry and Biochemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, Email:

B. L. Nilsson, L. L. Kiessling, R. T. Raines, Org. Lett., 2001, 3, 9-12.

DOI: 10.1021/ol006739v

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The Staudinger ligation can be used to couple a peptide with a C-terminal phosphinothioester to another with an N-terminal α-azido group to form a single peptide that contains no residual atoms.

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proposed mechanism

Key Words

Staudinger reaction, Amides

ID: J54-Y2001