Development of Highly Potent D-Glucosamine-Based Chiral Fluorescent Labeling Reagents and a Microwave-Assisted .BETA.-Selective Glycosidation of a Methyl Glycoside Reagent

• OHRUI Hiroshi

  Graduate School of Life Sciences, Tohoku University

• KATO Rumiko

  Graduate School of Life Sciences, Tohoku University

• KODAIRA Teruhisa

  Graduate School of Life Sciences, Tohoku University

• SHIMIZU Hiroki

  Graduate School of Life Sciences, Tohoku University National Institute of Advanced Industrial Science and Technology (AIST), Hokkaido Center

• AKASAKA Kazuaki

  Graduate School of Life Sciences, Tohoku University

• KITAHARA Takeshi

  Kitasato Institute

Bibliographic Information

Other Title

• Development of Highly Potent D-Glucosamine-Based Chiral Fluorescent Labeling Reagents and a Microwave-Assisted β-Selective Glycosidation of a Methyl Glycoside Reagent
• Development of Highly Potent D Glucosamine Based Chiral Fluorescent Labeling Reagents and a Microwave Assisted ベータ Selective Glycosidation of a Methyl Glycoside Reagent
• Development of Highly Potent<scp>D</scp>-Glucosamine-Based Chiral Fluorescent Labeling Reagents and a Microwave-Assisted β-Selective Glycosidation of a Methyl Glycoside Reagent
• Development of Highly Potent D-Glucosamine-Based Chiral Fluorescent Labeling Reagents and a Microwave-Assisted β-Selective Glycosylation of a Methyl Glycoside Donor

Abstract

We synthesized new chiral fluorescence labeling reagents having a 2,3-anthracenedicarboximide group from D-glucosamine, and it was possible to introduce target alcohols at the anomeric positions of the reagents with β-selectivity by glycosidations. Especially, it was possible to use methyl glycoside reagent as a glycosyl donor with a Lewis acid and microwave irradiation, and it gave selectively β-glycoside while the reaction without microwave irradiation gave α- and β-mixed glycosides. Those reagents showed very high chiral discrimination ability, and they made it possible to separate the eight stereoisomers of 4,8,12,16-tetramethylheptadecanol by HPLC after derivatizations.

Journal

• Bioscience, Biotechnology, and Biochemistry

  Bioscience, Biotechnology, and Biochemistry 69 (5), 1054-1057, 2005

  Japan Society for Bioscience, Biotechnology, and Agrochemistry

Keywords

• glycosylation
• microwave
• methyl glycoside
• fluorescent reagent
• chiral discrimination

Details

• CRID: 1390282681451499520
• NII Article ID: 130000030345
• NII Book ID: AA10824164
• DOI: 10.1271/bbb.69.1054
• ISSN: 13476947
• ISSN: 09168451
• NDL BIB ID: 7322844
• PubMed: 15914934
• Web Site: http://id.ndl.go.jp/bib/7322844
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I7322844
• Web Site: http://www.tandfonline.com/doi/pdf/10.1271/bbb.69.1054
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
• Abstract License Flag: Disallowed