The synthesis and chemical properties of polyisoprenyl beta-D-mannopyranosyl phosphates.
2,3,4,6-Tetra-O-acetyl-beta-D-mannopyranosyl phosphate, free of the alpha anomer, was coupled with citronellol and dolichol in the presence of triisopropylbenzenesulfonyl chloride to give, after chromatographic purification and deacetylation, the respective polyisoprenyl beta-D-mannopyranosyl phosphates. These compounds were compared with the previously synthesized alpha anomers by means of their chromatographic properties, spectra, optical rotations, and hydrolysis reactions when treated with acid and alkali. To characterize the compounds resulting from these treatments, and to determine the mechanism of the alkaline hydrolysis, beta-D-mannopyranosyl phosphate was converted into beta-D-mannonpyranose 1,2-phosphate, and hence into D-mannose 2-phosphate, obtained as a mixture of alpha and beta anomers, characterized by infrared and nuclear magnetic resonance spectra and elemental analysis. Beta-D-Mannopyranosyl phosphate was readily separated by thin layer chromatography from the corresponding alpha anomer.
D002855:Chromatography, Thin Layer; D006600:Hexosephosphates / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008358:Mannose / Q000031:analogs & derivatives; D008722:Methods; D009904:Optical Rotation; D010743:Phospholipids / Q000138:chemical synthesis; D013055:Spectrophotometry, Infrared; D013729:Terpenes / Q000138:chemical synthesis*
D006600:Hexosephosphates; D010743:Phospholipids; D013729:Terpenes; D008358:Mannose