Fatty acid steryl, stanyl, and steroid esters by esterification and transesterification in vacuo using Candida rugosa lipase as catalyst.
Sterols (sitosterol, cholesterol, stigmasterol, ergosterol, and 7-dehydrocholesterol) and sitostanol have been converted in high to near-quantitative yields to the corresponding long-chain acyl esters via esterification with fatty acids or transesterification with methyl esters of fatty acids or triacylglycerols using lipase from Candida rugosa as biocatalyst in vacuo (20-40 mbar) at 40 degrees C. Neither organic solvent nor water is added in these reactions. Under similar conditions, cholesterol has been converted to cholesteryl butyrate and steroids (5alpha-pregnan-3beta-ol-20-one or 5-pregnen-3beta-ol-20-one) have been converted to their propionic acid esters, both in moderate to high yields, via transesterification with tributyrin and tripropionin, respectively. Reaction parameters studied in esterification include the temperature and the molar ratio of the substrates as well as the amount and reuse properties of the C. rugosa lipase. Lipases from porcine pancreas, Rhizopus arrhizus, and Chromobacterium viscosum are quite ineffective as biocatalysts for the esterification of cholesterol with oleic acid under the above conditions.
Weber
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N
Institute for Biochemistry and Technology of Lipids, H. P. Kaufmann-Institute, Federal Centre for Cereal, Potato and Lipid Research, Piusallee 68, D-48147 Münster, Germany.
Weitkamp
P
P
Mukherjee
K D
KD
D002175:Candida / Q000201:enzymology*; D002384:Catalysis; D002784:Cholesterol / Q000378:metabolism; D003684:Dehydrocholesterols / Q000378:metabolism; D004875:Ergosterol / Q000378:metabolism; D004951:Esterification; D005227:Fatty Acids / Q000378:metabolism*; D007700:Kinetics; D008049:Lipase / Q000378:metabolism*; D012855:Sitosterols / Q000378:metabolism; D013261:Sterols / Q000378:metabolism*; D013265:Stigmasterol / Q000378:metabolism; D013379:Substrate Specificity; D014280:Triglycerides / Q000378:metabolism; D014618:Vacuum
D003684:Dehydrocholesterols; D005227:Fatty Acids; D012855:Sitosterols; D013261:Sterols; D014280:Triglycerides; C025473:gamma-sitosterol; D002784:Cholesterol; D013265:Stigmasterol; C016705:7-dehydrocholesterol; C021255:stigmastanol; D008049:Lipase; D004875:Ergosterol