Total synthesis of chain-length-uniform dolichyl phosphates and their fitness to accept hexoses in the enzymatic formation of lipoglycans

Biological Chemistry Hoppe-Seyler
L Jaenicke, H U Siegmund

Abstract

Dolichols of defined uniform chain length (C35, C45, and C55) and geometry were prepared by total synthesis according to the following principle: (E,E)-Farnesol, activated as its 4-tolyl sulfone, is condensed with 8-chloroneryl benzyl ether, the sulfonyl group removed and the ether linkage cleaved by lithium/triethylamine. The resulting elongated prenol is converted again to its corresponding 4-toly/sulfone; at this stage isomers are removed by chromatography. After several cycles of this C10-elongation sequence the synthesis is completed in the same way but using 8-chlorocitronellyl benzyl ether as building block to introduce the saturated alpha-isoprene unit. The dolichols obtained were chemically phosphorylated (POCl3/Et3N). Both, the alcohols and their phosphate esters, are characterized spectroscopically. 1H- and 13C-NMR data are recorded for qualitative and stereochemical comparison with natural dolichols. The authentic dolichyl phosphates (Dol-7-P, Dol-9-P, and Dol-11-P) were assayed relative to the natural dolichyl phosphate mixture from pig liver as acceptors for transglycosylation from nucleoside diphosphate sugars (glucose, mannose) by standardized membrane vesicle preparations from plants (Volvox) and animals (liver...Continue Reading

References

Aug 4, 1972·Biochimica Et Biophysica Acta·W J Lennarz, M G Scher
Feb 7, 1967·Biochimica Et Biophysica Acta·P J DunphyJ Feeney
Apr 1, 1982·CRC Critical Reviews in Biochemistry·R J Staneloni, L F Leloir
Jan 1, 1983·Archives of Biochemistry and Biophysics·E BauseL Jaenicke
Jun 1, 1960·The Journal of Biophysical and Biochemical Cytology·Y MOULEJ CHAUVEAU

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