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The Mercaptomethyl Group Facilitates an Efficient One-Pot Ligation at Xaa-Ser/Thr for (Glyco)peptide Synthesis

Authors

  • Hironobu Hojo Prof. Dr.,

    1. Department of Applied Biochemistry, Institute of Glycoscience, Tokai University, 1117 Kitakaname, Hiratsuka, Kanagawa 259-1292 (Japan), Fax: (+81) 463-50-2075
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  • Chinatsu Ozawa,

    1. Department of Applied Biochemistry, Institute of Glycoscience, Tokai University, 1117 Kitakaname, Hiratsuka, Kanagawa 259-1292 (Japan), Fax: (+81) 463-50-2075
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  • Hidekazu Katayama Dr.,

    1. Department of Applied Biochemistry, Institute of Glycoscience, Tokai University, 1117 Kitakaname, Hiratsuka, Kanagawa 259-1292 (Japan), Fax: (+81) 463-50-2075
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  • Akiharu Ueki Dr.,

    1. Department of Applied Biochemistry, Institute of Glycoscience, Tokai University, 1117 Kitakaname, Hiratsuka, Kanagawa 259-1292 (Japan), Fax: (+81) 463-50-2075
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  • Yuko Nakahara Dr.,

    1. Department of Applied Biochemistry, Institute of Glycoscience, Tokai University, 1117 Kitakaname, Hiratsuka, Kanagawa 259-1292 (Japan), Fax: (+81) 463-50-2075
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  • Yoshiaki Nakahara Prof. Dr.

    1. Department of Applied Biochemistry, Institute of Glycoscience, Tokai University, 1117 Kitakaname, Hiratsuka, Kanagawa 259-1292 (Japan), Fax: (+81) 463-50-2075
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  • This work was supported by a grant-in-aid for creative scientific research from the Japan Society for the Promotion of Science (17GS0420), and in part by a grant-in-aid for scientific research from the Ministry of Education, Sports, Science, and Technology of Japan (20380069). We thank Tokai University for their support with a grant-in-aid for high technology research. We also thank Prof. Hiromichi Nagasawa and Shinji Nagata of Tokyo University for sequence analysis and Tsuyoshi Ohira of Kanagawa University for providing Glu-C. Xaa=any amino acid.

Abstract

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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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