The preparation of the four monophosphates of α,α′-trehalose from trehalose and sodium phosphate

✍ Scribed by Edward Tarelli; Susan F. Wheeler

• Publisher: Elsevier Science
• Year: 1994
• Tongue: English
• Weight: 812 KB
• Volume: 261
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(94)80003-0

✦ Synopsis

cY,cu'-Trehalose, when dried to a moisture content of ca. 5% from aqueous sodium phosphate buffer (with an initial pH I 5.5), produces, after warming, a mixture containing the four isomeric monophosphate esters which can be isolated by anion-exchange chromatography. Their structures were deduced from their hydrolysis products (trehalose and inorganic orthophosphate) after treatment with alkaline phosphomonoesterase, and by 'H and 13C NMR spectroscopy which, in the case of the 6-isomer, gave spectra identical with those of authentic material. Under similar conditions, other saccharides, including glucose, sucrose, amylose, cyclodextrins, alditols and cyclitols (e.g., glycerol, mannitol, and inositol), also produce (as shown by chromatographic and enzymic analyses and, in some instances, from spectroscopic analysis of isolated products) their corresponding phosphate esters. The presence of higher phosphorylated species is indicated in chromatograms of the mixtures, especially when metaphosphate is used as the phosphorylating agent. The methodology described provides a simple and direct route to such phosphate esters.