Synthetic Studies on Oligosaccharide Mimics Carrying Sulfur Atoms in the Pyranose Rings

• Hashimoto Masaru

  Faculty of Agriculture and Lifescience, Hirosaki University

Bibliographic Information

Other Title

• ピラノース環酸素を硫黄原子で置換したチオオリゴサッカリドの合成研究
• ピラノースカン サンソ オ イオウ ゲンシ デ チカン シタ チオオリゴサッカリド ノ ゴウセイ ケンキュウ

Abstract

This paper describes the synthetic studies of sulfur substituted oligosaccharides performed in our laboratory. Efficient and α-selective glycosidation reactions with 5-thiopyranoses were realized employing 1-O-trichloroacetimidates of 5-thiopyranoses carrying 2-OΟ-etheral protective groups. These conditions were applied for the synthesis of sulfur substituted maltose and isothiomaltose derivatives. The Pummerer rearrangement of 2, 3-O-isopropylidene protected 1-dehydrothiopyranose oxide was found to proceed at the C 1 position regioselectively to provide 5-thiopyranose derivative. Experiments employing labeled compound revealed the reaction mechanism. Development of 3-cyano-3-tert-butyldimethylsilyl-propyl (CSP group) thioether brought us an successful synthesis of sulfur substituted galacturonic acid. Enzymatic properties of these analogue against endo-glycosidases are also described.

Journal

• Journal of Synthetic Organic Chemistry, Japan

  Journal of Synthetic Organic Chemistry, Japan 64 (7), 766-777, 2006

  The Society of Synthetic Organic Chemistry, Japan

Keywords

• endo-glycosidase
• investigation of reaction mechanism
• sulfur analogues of oligosaccharides
• glycosylation reaction
• the Pummerer reaction
• polygalacturonase
• 3-cyano-3-tert-butyldimethylsilylpropyl (CSP) group
• molecular dynamic simulations

Details

• CRID: 1390001205312933760
• NII Article ID: 10017618022
• NII Book ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.64.766
• ISSN: 18836526
• ISSN: 00379980
• NDL BIB ID: 8032405
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I8032405
• Text Lang: ja
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed