Stereochemical Differentiation in the Simmons-Smith Reaction for Cyclopropanated Glucopyranose Derivatives as Molecular Probes for Glycosidases

• AKIYAMA Nanako

  Faculty of Agriculture and Life Science, Hirosaki University

• NOGUCHI Shogo

  Faculty of Agriculture and Life Science, Hirosaki University

• HASHIMOTO Masaru

  Faculty of Agriculture and Life Science, Hirosaki University

Abstract

Glucopyranose analogues carrying a bicyclo[4.1.0]heptane framework (4) and the diastereomer of the cyclopropane moiety were synthesized as the unit for molecular probes to mimic the unstable transition state conformation of the glucopyranose ring in enzymatic hydrolysis. The synthesis features differentiation of the α- and β-stereoselectivity in cyclopropanation of the corresponding cyclohexene derivative (5).

Journal

• Bioscience, Biotechnology, and Biochemistry

  Bioscience, Biotechnology, and Biochemistry 75 (7), 1380-1382, 2011

  Japan Society for Bioscience, Biotechnology, and Agrochemistry

Keywords

• cyclopropane
• glucopyranose
• Simmons-Smith reaction
• stereoselectivity
• transition state analogue

Details

• CRID: 1390001206476983680
• NII Article ID: 10029329535
• NII Book ID: AA10824164
• DOI: 10.1271/bbb.110120
• ISSN: 13476947
• ISSN: 09168451
• NDL BIB ID: 11175230
• PubMed: 21737920
• Web Site: http://id.ndl.go.jp/bib/11175230
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I11175230
• Web Site: http://www.tandfonline.com/doi/pdf/10.1271/bbb.110120
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed