title: Fungal biotransformation of (+/-)-linalool.
abstract: The biotransformation of (+/-)-linalool was investigated by screening 19 fungi. Product accumulation was enhanced by substrate feeding and, for the first time, lilac aldehydes and lilac alcohols were identified as fungal biotransformation byproduct using SPME-GC-MS headspace analysis. Aspergillus niger DSM 821, Botrytis cinerea 5901/02, and B. cinerea 02/FBII/2.1 produced different isomers of lilac aldehyde and lilac alcohol from linalool via 8-hydroxylinalool as postulated intermediate. Linalool oxides and 8-hydroxylinalool were the major products of fungal (+/-)-linalool biotransformations. Furanoid trans-(2 R,5 R)- and cis-(2 S,5 R)-linalool oxide as well as pyranoid trans-(2 R,5 S)- and cis-(2 S, 5 S)-linalool oxide were identified as the main stereoisomers with (3 S,6 S)-6,7-epoxylinalool and (3 R,6 S)-6,7-epoxylinalool as postulated key intermediates of fungal (+/-)-linalool oxyfunctionalization, respectively. With a conversion yield close to 100% and a productivity of 120 mg/L.day linalool oxides, Corynespora cassiicola DSM 62485 was identified as a novel highly stereoselective linalool transforming biocatalyst showing the highest productivity reported so far.
authors.affiliation: DECHEMA e.V., Karl-Winnacker-Institut, Biochemical Engineering, PO Box 150104, D-60061 Frankfurt/Main, Germany.
authors.forename: Marco-Antonio
authors.initials: MA
authors.lastname: Mirata
authors.forename: Matthias
authors.initials: M
authors.lastname: Wüst
authors.forename: Armin
authors.initials: A
authors.lastname: Mosandl
authors.forename: Jens
authors.initials: J
authors.lastname: Schrader
mesh_terms: D000080462:Acyclic Monoterpenes; D000438:Alcohols / Q000378:metabolism; D000447:Aldehydes / Q000378:metabolism; D001203:Ascomycota / Q000378:metabolism; D001234:Aspergillus niger / Q000378:metabolism; D020171:Botrytis / Q000378:metabolism; D035264:Flowers / Q000737:chemistry; D005658:Fungi / Q000254:growth & development / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D005947:Glucose / Q000378:metabolism; D007700:Kinetics; D039821:Monoterpenes / Q000378:metabolism*; D013237:Stereoisomerism; D031662:Syringa / Q000737:chemistry
chemical_list: D000080462:Acyclic Monoterpenes; D000438:Alcohols; D000447:Aldehydes; D039821:Monoterpenes; C018584:linalool; D005947:Glucose