The selective enzymatic synthesis of lipophilic esters of swainsonine

The potent and specific inhibitor of Golgi alpha-mannosidase II, swainsonin e (SW) has been isolated in high yield from Swainsona procumbens and deriva tised by regiospecific enzymatic reactions. In this study the regioselectiv ity of three commercially available enzymes, subtilisin Carlsberg, porcine pancreatic lipase (PPL) and Candida cylindracea lipase was determined for t he acylation of swainsonine in predominantly anhydrous organic medium. The use of subtilisin in pyridine facilitated the single step synthesis of 2-O- butyryl-SW in a 23% yield, whilst catalysis by PPL in tetrahydrofuran gave 2-O-butyryl-SW (6%) and 1,2-di-O-butyryl-SW (31%). (C) 1999 Elsevier Scienc e Ltd. All rights reserved.