Constituents of Holothuroidea, 16. Determination of Absolute Configuration of the Branched Methyl Group in Ante-iso Type Side Chain Moiety on Long Chain Base of Glucocerebroside from the Sea Cucumber Holothuria leucospilota

• Yamada Koji

  Faculty of Pharmaceutical Sciences, Kyushu University

• Onaka Hiroyuki

  Faculty of Pharmaceutical Sciences, Kyushu University

• Tanaka Masakazu

  Faculty of Pharmaceutical Sciences, Kyushu University

• Inagaki Masanori

  Faculty of Pharmaceutical Sciences, Kyushu University

• Higuchi Ryuichi

  Faculty of Pharmaceutical Sciences, Kyushu University

Abstract

The absolute configuration of the branched methyl group in ante-iso type side chain moiety on the long chain base of glucocerebroside, HLC-2-A, which was isolated from the sea cucumber Holothuria leucospilota was determined. Oxidation of the glucocerebroside with ozone afforded C₁₃-fragment including the ante-iso moiety. The optically active C₁₃-fragment was synthesized asymmetrically by using the Wittig reaction from chiral synton for comparison with the natural fragment.

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 53 (10), 1333-1334, 2005

  The Pharmaceutical Society of Japan

Keywords

• glycosphingolipid
• glucocerebroside
• absolute configuration
• sea cucumber
• <i>Holothuria leucospilota</i>

Details

• CRID: 1390282679146126336
• NII Article ID: 110003666271
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.53.1333
• ISSN: 13475223
• ISSN: 00092363
• PubMed: 16204996
• Web Site: http://www.jstage.jst.go.jp/article/cpb/53/10/53_10_1333/_pdf
• Text Lang: en
• Data Source:
  • JaLC
  • Crossref
  • PubMed
  • CiNii Articles
• Abstract License Flag: Disallowed