Gas Chromatographic Separation of Carbohydrate Enantiomers on a New Chiral Stationary Phase

Abstract

The direct separation of simple, volatile derivatives of enantiomeric sugars has been achieved for the first time by glass‐capillary gas chromatography of trifluoroacetyl derivatives on a temperature‐stable, chiral stationary phase. The usefulness of the new method was demonstrated on an hydrolyzate of the galactan of the snail Helix pomatia.

Antiprotozoal Steroidal Saponins from the Marine Sponge Pandaros acanthifolium

“…Their structures were determined on the basis of extensive spectroscopic analyses, including two-dimensional NMR and HRESIMS data. As the previously isolated pandarosides A-D (13)(14)(15)(16), the new compounds 1-12 share an unusual oxidized D-ring and a cis C/D ring junction. The absolute configurations of the aglycones were assigned by interpretation of CD spectra, whereas the absolute configurations of the monosaccharide units were determined by chiral GC analyses of the acid methanolysates.…”

“…12 The same chiral GC analysis allowed us to propose the usual L absolute configuration for this sugar. 13 Compound 6 exhibited the molecular formula HMBC correlations. The configuration of this C=C double bond was assigned as Z due to a nOe between H-24 1 and H 3 -26.…”

“…During our first investigation of the little-studied Caribbean marine sponge Pandaros acanthifolium (Poecilosclerida, Microcionidae) collected at the Canyon rock off the Martinique coast, steroidal saponins named pandarosides A-D (13)(14)(15)(16), as well as their methyl esters (17)(18)(19), were identified as the major constituents of the sponge extract. 4 Before that, saponins have mostly been isolated from marine sponge of the genera Asteropus and Erylus.…”

Derivatization of carbohydrates for GC and GC–MS analyses

“…Konig et al [194] introduced pentylated ␣-cyclodextrin as a chiral stationary phase for GC separation of enantiomeric carbohydrates. Numerous monosaccharides, anhydroalditols, polyols and other compounds were trifluoroacetylated and readily separated on this column.…”

Acanthifoliosides, minor steroidal saponins from the Caribbean sponge Pandaros acanthifolium

“…The D absolute configuration of xylose was obtained by chiral GC analysis of the acetylated sugar residue after acid methanolysis of 1. 14…”