Abstract
The methanolyzed lipids of the extreme halophile, Halobacterium cutirubrum, were separated into glycerol diether and glycerol monoether fractions. The diether was shown by synthesis to be 2,3-di-O-(3'R,7'R,11'R,15'-tetramethylhexadecyl)-sn-glycerol. The monoether fraction was separated by thin-layer chromatography on boric acid-impregnated silicic acid into about equal amounts of alpha- and -isomers. The alpha-isomer was found to be identical with the synthetic 3-O-(3'R,7'R,11'R,15'-tetramethylhexadecyl)-sn-glycerol, and the -isomer was identical with the synthetic 2-O-(3'R,7'R,11'R,15'-tetramethylhexadecyl) glycerol.
Highlights
The methanolyzed lipids of the extreme halophile, Halobacterium cutirubrum, were separated into glycerol diether and glycerol monoether fractions
The acetone-insoluble lipids (4.9 g) were methanolyzed (1) in 100 ml of 2.5% anhydrous methanolic hydrogen chloride under reflux for 4-5 hr; the mixture was diluted with 10 ml of water, and the crude glycerol diether, together with small amounts of glycerol monoethers (3) was extracted with several 50-ml portions of petroleum ether
The chloro compound was identified by comparison of its R, values on TLC and relative retentions on Gas--liquid chromatography (GLC) with those of the authentic synthetic substance; it was probably formed from the diether during the refluxing with niethanolic HCl
Summary
The methanolyzed lipids of the extreme halophile, Halobacterium cutirubrum, were separated into glycerol diether and glycerol monoether fractions. The diether was shown by synthesis to be 2,3-di-O-(3‘R,7’R,ll’R,15’-tetramethylhexadecy1)-sn-glycerol. The monoether fraction was separated by thin-layer chromatography on boric acid-impregnated silicic acid into about equal amounts of a- and j3isomers. The a-isomer was found to be identical with the synthetic 3-0-(3’R,7’R,ll ’R,15’-tetramethylhexadecy1)-snglycerol, and the j3-isomer was identical with the synthetic 2-0-(3’R,7’R,11’R,15’-tetramethylhexadecyl) glycerol
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