Structure of a Major Glycophosphoceramide from Tobacco Leaves, PSL-I: 2-Deoxy-2-acetamido-d-glucopyranosyl(α1→4)-D-glucuronopyranosyl(α1→2)myoinositol-1 -O-phosphoceramide

Thomas C.Y. Hsieh, University of Kentucky College of Medicine
Roger A. Laine, University of Kentucky College of Medicine
Robert L. Lester, University of Kentucky College of Medicine
Karan Kaul, University of Colorado Boulder

Abstract

The chemical structure of a major glycophosphoceramide from tobacco leaves, called PSL-I [K. Kaul and R. L. Lester (1975), Plant Physiol. 55, 120], has now been characterized as 2-deoxy-2-acetamido-d-glucopyranosyl-(α1→4)D-glucuronopyranosyl(α1 →myoinositol-1 -O-phosphoceramide. Sites of glycosidic linkage were determined by (1) methylation analysis on a trisaccharide isolated by degradation of carboxyl-reduced PSL-I and (2) periodate oxidation experiments on PSL-I. The resulting products were identified with gas chromatography/mass spectrometry. Anomeric configurations were determined by resistance of the sugars in the peracetylated trisaccharide to chromium trioxide treatment. © 1978, American Chemical Society. All rights reserved.