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Second-Generation Sugar-Assisted Ligation: A Method for the Synthesis of Cysteine-Containing Glycopeptides

Authors

  • Simon Ficht,

    1. The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-748-2409
    2. Academia Sinica, Taipei, Taiwan
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    • S. Ficht and R. J. Payne contributed equally.

  • Richard J. Payne,

    1. The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-748-2409
    2. Academia Sinica, Taipei, Taiwan
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    • S. Ficht and R. J. Payne contributed equally.

  • Ashraf Brik Dr.,

    1. Department of Chemistry, Ben Gurion University, Beer Sheva, Israel
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  • Chi-Huey Wong Prof.

    1. The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-748-2409
    2. Academia Sinica, Taipei, Taiwan
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  • This work was supported by the NIH and the Skaggs Institute for Chemical Biology. S.F. is grateful to the Deutsche Akademische Austauschdienst (DAAD) for a postdoctoral fellowship. R.J.P. is grateful for funding provided by the Lindemann Trust Fellowship.

Abstract

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Sweet ligations: A second-generation sugar-assisted ligation is described that incorporates a sugar moiety with an ester-linked thiol auxiliary. Efficient auxiliary removal leads to native glycopeptides without the use of protecting groups. Extended glycopeptides also facilitate efficient ligation reactions by this method, therefore making it possible to scan a target sequence until a synthetically viable ligation junction is found.

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