Planta Med 2012; 78 - PK3
DOI: 10.1055/s-0032-1321319

Synthetic studies of MA026, A novel antiviral lipocyclodepsipeptide

S Shimura 1, M Ishima 1, I Ota 1, E Tsutsui 1, S Kamisuki 1, H Murata 1, T Yamazaki 1, T Suzuki 2, K Kuramochi 3, T Takeuchi 1, K Watashi 4, S Kobayashi 2, F Sugawara 1
  • 1Faculty of Science and Technology
  • 2Faculty of Pharmaceutical Science, Tokyo University of Science, Noda, 278–8510, Japan
  • 3Graduate School of Life and Environmental Science, Kyoto Prefectural University, Kyoto, 606–8522, Japan
  • 4National Institute of Infectious Diseases, Tokyo, 162–8640, Japan

MA026, a novel lipocyclodepsipeptide, exhibits multiple antiviral activity, and its mode of action is unrevealed. MA026 has the potential to create a novel antiviral drug and thus more biological characterizations are required. To accomplish the biological investigation, a flexible chemical synthesis is essential. MA026 consists of (R)-3-hydroxydecanoic acid, linear peptide and cyclodepsipeptide. To maximize the convergency, MA026 was devided into three segments: branched cyclodepsipeptide 2, tripeptide 3 and fatty acid moiety 4. Macrocyclization of depsipeptide is a key step in the total synthesis, so we chose two macrocyclization sites (A) and (B). Here, we present synthetic studies of MA026.