Synthetic Studies of plusbacin A3

DOI

Bibliographic Information

Other Title
  • Joullie-Ugi反応を用いたplusbacin A3の合成研究

Abstract

<p>Plusbacin A3, which was isolated from Pseudomonas sp. PB-6250 obtained from a soil sample collected in the Okinawa Prefecture, Japan, has five nonproteinogenic amino acids, allo-D-threonine, trans-3-hydroxy-L-proline, L-threo-b-hydroxy-aspartic acid, and D-threo-b-hydroxy-aspartic acid. Plusbacin A3 exhibits a potent antibacterial activity against drug-resistant pathogens including Methicillin-resistant S. aureus (MRSA) and vancomycin-resistant enterococci (VRE). Since the mode of action of plusbacin A3 differs from existing antibacterial drug, plusbacin A3is expected to be a lead compound as a novel antibacterial drug.</p><p>We planned to synthesize plusbain A3considering to develop more convergent synthetic route, which can be applicable to structure-activity relationship. Our retro-synthetic analysis of plusbacin A3 is depicted as follows. Segment A was synthesized from isocyanide 14, imine 2, and carboxylic acid 15, and segment B was synthesized from isocyanide 13 imine 2, and carboxylic acid 12 via Joullie-Ugi reaction. Then, esterification of segment A and segment B afford trace amount of cyclization precursor 34. </p>

Journal

Details 詳細情報について

  • CRID
    1390282763021770496
  • NII Article ID
    130007399556
  • DOI
    10.24496/tennenyuki.56.0_poster52
  • ISSN
    24331856
  • Text Lang
    ja
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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