Enantioselective monoterpene alcohol acetylation in Origanum, Mentha and Salvia species.
Selected plants within the Origanum, Mentha and Salvia genera, that contain significant amounts of chiral volatile alcohols and their related acetates, exhibit remarkable enantioselectivity of alcohol acetyl transferase (AAT) activity and particularly can discriminate between linalool enantiomers. Origanum dayi AAT produced almost enantiomerically pure (R)-linalyl acetate by enzymatic acetylation of racemic linalool, whereas the closely related O. majorana AAT produced a mixture of (R)- and (S)-linalyl acetate with a ratio of 6:4. V(max) of O. dayi acetylation activity was 30-fold higher for (R)-linalool, whereas in O. majorana no such differences were found.
Department of Vegetable Crops, Agricultural Research Organization (ARO), Newe Ya'ar Research Center, P.O. Box 1021, Ramat Yishay 30095, Israel.
Olga
O
Larkov
Alon
A
Zaks
Einat
E
Bar
Efraim
E
Lewinsohn
Nativ
N
Dudai
Alfred M
AM
Mayer
Uzi
U
Ravid
D000107:Acetylation; D000123:Acetyltransferases / Q000378:metabolism*; D000080462:Acyclic Monoterpenes; D000438:Alcohols / Q000378:metabolism*; D027541:Mentha / Q000201:enzymology*; D015394:Molecular Structure; D039821:Monoterpenes / Q000378:metabolism*; D009822:Oils, Volatile / Q000378:metabolism; D031341:Origanum / Q000201:enzymology*; D018515:Plant Leaves / Q000378:metabolism; D027544:Salvia / Q000201:enzymology*; D013379:Substrate Specificity; D055549:Volatile Organic Compounds
D000080462:Acyclic Monoterpenes; D000438:Alcohols; D039821:Monoterpenes; D009822:Oils, Volatile; D055549:Volatile Organic Compounds; C074463:linalyl acetate; C018584:linalool; D000123:Acetyltransferases