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Hironobu Hojo, Chinatsu Ozawa, Hidekazu Katayama, Akiharu Ueki, Yuko Nakahara and Yoshiaki Nakahara The Mercaptomethyl Group Facilitates an Efficient One-Pot Ligation at Xaa-Ser/Thr for (Glyco)peptide Synthesis Angewandte Chemie International Edition 49

Article first published online: 7 JUL 2010 | DOI: 10.1002/anie.201000384

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Going native: A mercaptomethyl group on the side-chain hydroxy group of serine and threonine residues facilitates a native chemical ligation reaction at the Xaa-Ser/Thr site (see scheme; R=H or Me). The intermediate thioester is treated to achieve an S- to N-acyl shift. After ligation, the group is spontaneously removed to obtain the glycopeptide contulakin-G and human calcitonin.

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