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Late-stage stitching enabled by manganese-catalyzed C─H activation: Peptide ligation and access to cyclopeptides

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Science Advances  26 Feb 2021:
Vol. 7, no. 9, eabe6202
DOI: 10.1126/sciadv.abe6202
  • Table 1 Optimization studies for the hydroarylation with tryptophan 1a.

    Exploration of solvent, additive, and temperature effects on the hydroarylation of alkynes with tryptophan derivative 1a.


    Embedded Image
    EntryRSolventTemperature (°C)Yield (%)
    1R1toluene10037
    2R1DCE10083
    3R1DME10097
    4R11,4-dioxane10098
    5R1DMF100
    6R1H2O10043
    7R11,4-dioxane8097
    8R11,4-dioxane6097
    9R11,4-dioxane4058
    10R11,4-dioxane6085*
    11R11,4-dioxane60
    12R11,4-dioxane60
    13R11,4-dioxane6097§
    14R21,4-dioxane6086
    15R21,4-dioxane8090
    16R21,4-dioxane10095

    Reaction conditions: 1a (0.15 mmol), 2 (0.23 mmol), MnBr(CO)5 (10 mol %), NaOAc (30 mol %), solvent (0.6 ml), 16 hours. Yields of isolated product.

    *Without NaOAc.

    †Without MnBr(CO)5.

    ‡Boc-Trp-OMe (0.15 mmol) in lieu of 1a.

    §1-(pyridin-2-yl)-1H-indole (0.15 mmol) in lieu of 1a.

    Supplementary Materials

    • Supplementary Materials

      Late-stage stitching enabled by manganese-catalyzed C—H activation: Peptide ligation and access to cyclopeptides

      Nikolaos Kaplaneris, Felix Kaltenhӓuser, Giedre Sirvinskaite, Shuang Fan, Tiago De Oliveira, Lena-Christin Conradi, Lutz Ackermann

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      • Supplementary Materials and Methods
      • Supplementary Text
      • Figs. S1 and S2
      • References

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