An improved procedure for the preparation of alkyl sulphate esters suitable for the study of secondary alkylsulphohydrolase enzymes.
A simple, rapid and convenient method for the synthesis of secondary alkyl sulphate esters is described in which the sodium alkoxide of the parent alcohol is sulphated by using triethylamine-SO3 complex. The procedure gives relatively good yields, even for the sulphation of long-chain alcohols and those in which the hydroxy group is remote from the terminal carbon atoms. Positional isomerization, arising from the migration of the hydroxy group along the carbon chain, is absent, and resolved enantiomers of alcohols react with complete retention of configuration.
D000438:Alcohols / Q000032:analysis; D002849:Chromatography, Gas; D005021:Ethylamines; D006868:Hydrolysis; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D011549:Pseudomonas / Q000201:enzymology; D013429:Sulfatases / Q000378:metabolism*; D013463:Sulfuric Acid Esters / Q000138:chemical synthesis*; D013464:Sulfuric Acids / Q000138:chemical synthesis*
D000438:Alcohols; D005021:Ethylamines; D013463:Sulfuric Acid Esters; D013464:Sulfuric Acids; D013429:Sulfatases