4.8 Article

Native Chemical Ligation at Glutamine

Journal

ORGANIC LETTERS
Volume 14, Issue 6, Pages 1520-1523

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol300254y

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Funding

  1. Israel Ministry of Science and Technology
  2. Swiss Federal Institute of Technology-Lausanne (EPFL)

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The desulfurization reaction introduced by Van and Dawson as a postnative chemical ligation step greatly expanded the scope of ligation chemistry beyond Xaa-Cys (Xaa is any amino acid) by making ligation at Xaa-Phe, Xaa-Val, Xaa-Lys, Xaa-Leu, Xaa-Thr, and Xaa-Pro junctions accessible in the synthesis of functional proteins. A new ligation site based on Xaa-Gln utilizing gamma-mercaptoglutamine is reported, and several examples on the efficiency of ligation coupled with desulfurization are provided.

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