Synthesis of Gerfelin and Related Analogous Compounds

• ISLAM Md. Sadequl

  Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo

• KITAGAWA Mitsuhiro

  Department of Biosciences and Informatics, Faculty of Science and Technology, Keio University

• IMOTO Masaya

  Department of Biosciences and Informatics, Faculty of Science and Technology, Keio University

• KITAHARA Takeshi

  Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo Center for Basic Research, The Kitasato Institute

• WATANABE Hidenori

  Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo

Abstract

Gerfelin, an inhibitor of human geranylgeranyl diphosphate (GGPP) synthase that has been isolated from a culture broth of Beauveria felina QN22047, was synthesized in 4 and 3 steps starting from 2,4-dihydroxy-6-methylbenzoic acid and 3,4,5-trihydroxytoluene, respectively. An effective ligand, 2-(di-tert-butylphosphino)biphenyl, was used in the palladium-catalyzed diaryl ether-forming reaction. Five analogous compounds of gerfelin were also synthesized for a study of the structure-activity relationship.

Journal

• Bioscience, Biotechnology, and Biochemistry

  Bioscience, Biotechnology, and Biochemistry 70 (10), 2523-2528, 2006

  Japan Society for Bioscience, Biotechnology, and Agrochemistry

Keywords

• gerfelin
• geranylgeranyl diphosphate synthase
• enzyme inhibitor

Details

• CRID: 1390001206477364992
• NII Article ID: 10018526100
• NII Book ID: AA10824164
• DOI: 10.1271/bbb.60287
• ISSN: 13476947
• ISSN: 09168451
• NDL BIB ID: 8524170
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I8524170
• Web Site: http://www.tandfonline.com/doi/pdf/10.1271/bbb.60287
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
• Abstract License Flag: Disallowed