Late-stage diversification of peptidomimetics and oligopeptides via gold-catalyzed post-Ugi cyclization

A chemo- and regioselective gold-catalyzed tandem 6-endo-dig cyclization/enyne cycloisomerization/1,2-migration process for the synthesis of decorated peptidomimetics is developed. Various migrating groups such as aryl, heteroaryl and alkyl are tolerated in this method under mild conditions. This protocol is successfully utilized to modify various oligopeptides, including substrates bearing the drug amantadine, in a rapid and step-economical manner through the combination with the Ugi reaction. © 2022 Elsevier B.V.

Authors
Song L.1, 2 , Liu C.1 , Tian G.1 , Van Meervelt L. , Van Der Eycken J. , Van Der Eycken E.V.
Journal
Molecular Catalysis
Publisher
Elsevier B.V.
Language
English
Status
Published
Link
External link
DOI
10.1016/J.MCAT.2022.112240
Number
112240
Volume
522
Year
2022
Organizations
  • 1 Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, KU Leuven Celestijnenlaan 200F, Leuven, 3001, Belgium
  • 2 Jiangsu Provincial Key Lab for the Chemistry and Utilization of Agro-Forest Biomass, Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Jiangsu Key Lab of Biomass-Based Green Fuels and Chemicals, International Innovation Center for Forest Chemicals and Materials, College of Chemical Engineering, Nanjing Forestry University, Jiangsu, Nanjing, 210037, China
  • 3 Biomolecular Architecture, Department of Chemistry, KU Leuven Celestijnenlaan 200F, Leuven, 3001, Belgium
  • 4 Laboratory for Organic and Bio-Organic Synthesis, Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281 (S.4), Ghent, 9000, Belgium
  • 5 Peoples’ Friendship University of Russia (RUDN University), Miklukho-Maklaya street 6, Moscow117198, Russian Federation
Keywords
Cyclization; Gold; Oligopeptide; Peptidomimetic; Post-Ugi
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