Lipase-catalysed resolution of gamma- and delta-lactones.
Lipase-catalysed stereoselective hydrolysis of a family of saturated gamma- and delta-lactones was investigated. Increasing the chain length from delta-octalactone to delta-dodecalactone leads to higher enantiomeric excess. Best results were found using a lipase from Pseudomonas species (KW51) yielding highest enantiomeric excesses (greater than 99% ee at 50% conversion, E > 100) at short reaction times (10 h) for delta-undecalactone and delta-dodecalactone. In contrast, gamma-lactones were resolved less efficiently. Highest enantioselectivities (70%ee at 50% conversion, E = 11) were found for gamma-nonalactone. Optimum reaction conditions were found at pH 8 and 12.5 degrees C.
Enzelberger
M M
MM
Institut für Technische Biochemie, Universität Stuttgart, Germany.
Bornscheuer
U T
UT
Gatfield
I
I
Schmid
R D
RD
D002175:Candida / Q000201:enzymology; D002861:Chromobacterium / Q000201:enzymology; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D007536:Isomerism; D007783:Lactones / Q000737:chemistry / Q000145:classification / Q000302:isolation & purification* / Q000378:metabolism; D008049:Lipase / Q000378:metabolism*; D015394:Molecular Structure; D011549:Pseudomonas / Q000201:enzymology*; D013696:Temperature
D007783:Lactones; D008049:Lipase