Enzymatic esterification of lavandulol--a partial kinetic resolution of (S)-lavandulol and preparation of optically enriched (R)-lavandulyl acetate.
The asymmetric esterification of the racemic primary alcohol lavandulol was achieved using lipase B from Candida antarctica and acetic acid as acyl donor in 80% yield. The enantioselectivity of the process was characterised, and a preparative resolution of 25 mM racemic lavandulol, stopped at approx. 55% conversion, yielded (S)-lavandulol in 42% yield and 52% e.e. and (R)-lavandulyl acetate in 51% yield and 48% e.e.
Cross
Hannah
H
York Structural Biology Laboratory, Department of Chemistry, University of York, Heslington, York YO10 5YW, UK.
Marriott
Ray
R
Grogan
Gideon
G
D000085:Acetates / Q000138:chemical synthesis*; D019342:Acetic Acid / Q000737:chemistry*; D000080462:Acyclic Monoterpenes; D000215:Acylation; D004789:Enzyme Activation; D004951:Esterification; D004952:Esters; D005656:Fungal Proteins; D007700:Kinetics; D008049:Lipase / Q000737:chemistry*; D039821:Monoterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D000085:Acetates; D000080462:Acyclic Monoterpenes; D004952:Esters; D005656:Fungal Proteins; D039821:Monoterpenes; D008049:Lipase; C431349:lipase B, Candida antarctica; C492922:lavandulyl acetate; D019342:Acetic Acid; C492921:lavandulol