The selective enzymatic synthesis of lipophilic esters of swainsonine.
The potent and specific inhibitor of Golgi alpha-mannosidase II, swainsonine (SW) has been isolated in high yield from Swainsona procumbens and derivatised by regiospecific enzymatic reactions. In this study the regioselectivity of three commercially available enzymes, subtilisin Carlsberg, porcine pancreatic lipase (PPL) and Candida cylindracea lipase was determined for the 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%).
Perrone
G G
GG
School of Biochemistry & Molecular Genetics, University of New South Wales, Sydney, Australia. g.perrone@unsw.edu.au
Barrow
K D
KD
McFarlane
I J
IJ
D002175:Candida / Q000201:enzymology; D004952:Esters / Q000138:chemical synthesis*; D008049:Lipase / Q000378:metabolism; D008956:Models, Chemical; D010179:Pancreas / Q000201:enzymology; D013381:Subtilisins / Q000378:metabolism; D017026:Swainsonine / Q000031:analogs & derivatives* / Q000302:isolation & purification
D004952:Esters; D008049:Lipase; D013381:Subtilisins; D017026:Swainsonine