Glycolipids from Sponges. 13.1 Clarhamnoside, the First Rhamnosylated α-Galactosylceramide from Agelas clathrodes. Improving Spectral Strategies for Glycoconjugate Structure Determination
- 22 January 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (4) , 1174-1179
- https://doi.org/10.1021/jo034865h
Abstract
Reinvestigation of the glycosphingolipid composition of the marine sponge Agelas clathrodes revealed the presence of a new tetraglycosylated α-galactoglycosphingolipid (1a), containing an unusual l-rhamnose unit in the sugar head. The structure of the new compound was elucidated using extensive 2D NMR studies. Because of the strong overlapping of the signals of the sugar protons in the 1H spectrum, 13C-coupled and 13C-decoupled phase-sensitive HMQC spectra were used to study the multiplicity of the overlapping signals. In addition, the absolute configuration of sugars was determined using a simple and efficient, yet underutilized CD method.Keywords
This publication has 6 references indexed in Scilit:
- The CD1 family and T cell recognition of lipid antigensTissue Antigens, 2002
- Population pharmacokinetics of the novel anticancer agent KRN7000Cancer Chemotherapy and Pharmacology, 2002
- Glycolipids from sponges. IV. Immunomodulating glycosyl ceramides from the marine sponge agelas dispar.Tetrahedron, 1996
- Agelasphins, novel antitumor and immunostimulatory cerebrosides from the marine sponge Agelas mauritianusTetrahedron, 1994
- Determination of the absolute configuration of the sugar residues of complex polysaccharides by circular dichroism spectroscopyAnalytical Biochemistry, 1989
- Carbon-13 NMR spectroscopy of steroidal sapogenins and steroidal saponinsPhytochemistry, 1985