Abstract
A sulfur-containing glycolipid, accounting for ca. 25% of the total polar lipids, has been isolated from the extreme halophile Halobacterium cutirubrum. The ammonium salt of the lipid was found to have the molecular formula C(61)H(117)O(21)S.NH(4), and on strong acid hydrolysis it yielded 2,3-di-O-phytanyl-sn-glycerol, glucose, mannose, galactose, and sulfate in equimolar proportions. Infrared and NMR spectra indicated the presence of a secondary sulfate group. Solvolysis of the lipid in 0.004 m HCl in tetrahydrofuran resulted in rapid release of inorganic sulfate and formation of galactosyl-mannosyl-glucosyl diphytanyl glycerol ether. With higher acid concentration (0.25 m methanolic HCl), stepwise hydrolysis of monosaccharide units occurred, giving mannosyl-glucosyl glycerol diphytanyl ether and monoglucosyl glycerol diphytanyl ether. The position of attachment of the sugars and of the sulfate group was determined by methylation of the free acid form of the glycolipid sulfate, followed by acid hydrolysis and gas-liquid chromatographic analysis of the partially methylated sugars as the alditol acetates. The configuration of the glycosidic linkages was established both by optical rotation measurements and by specific enzymatic hydrolysis. The results obtained established the structure as 2,3-di-O-phytanyl-1-O-[beta-d-galactopyranosyl-3'-sulfate-(1' -->6')-O-alpha-d-mannopyranosyl-(1' --> 2')-O-alpha-d-glucopyranosyl]-sn-glycerol.
Highlights
Di-0-phytanyl-sn-glycerol, glucosem, annoseg,alactose, and sulfatein equimolar proportions
The position of attachment of the sugarsand of the sulfate group was determined by methylation of the free acid form of the glycolipid sulfate, followed by acid hydrolysis and gas-liquid chromatographicanalysis of the partially methylated sugarsas the alditol acetates
In a preliminaryreport,Kateset al. (2) showed thatthis lipid wasasulfate ester of a triglycosyl diphytanyl glycerol ether.Thesugars were foundto beglucose, mannose, and galactose, and the linkages between them were determined; the sulfate group was found to be on the terminal sugar, galactose
Summary
Silica gel H, silica gel G, and kieselguhr G were obtainedfromBrinkmannInstruments(CanadaL) td., Rexdale, Ontario. Unisil silicic acid (200-325 mesh) was suppliedbyClarksonChemical Co., Williamsport,Pa. fl-Galactosidase Thi4s3is8an OpJeonuArcncaeslsoafrtLicliepuidndReretsheearCcChBYVliocleunmse.e 14,1973 coli) was obtained from WorthingtonBiochemical Corp., Freehold,N.J. All solvents were glass-distilled prior to use
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