Biocatalytic preparation and absolute configuration of enantiomerically pure fungistatic anti-2-benzylindane derivatives. Study of the detoxification mechanism by Botrytis cinerea.
Enantiomerically pure 2-benzylindane derivatives were prepared using biocatalytic methods and their absolute configuration determined. (1R,2S)-2-Benzylindan-1-ol ((1R,2S)-2) and (S)-2-benzylindan-1-one ((S)-3) were produced by fermenting baker's yeast. Lipase-mediated esterifications and hydrolysis of the corresponding racemic substrates gave rise to the enantiopure compounds (1S,2R)-2-benzylindan-1-ol ((1S,2R)-2) and (1R,2S)-2-benzylindan-1-ol ((1R,2S)-2), respectively. The antifungal activity of these products against two strains of the plant pathogen Botrytis cinerea was tested. The metabolism of anti-(+/-)-2-benzylindan-1-ol (anti-(+/-)-2) by B. cinerea as part of the fungal detoxification mechanism is also described and revealed interesting differences in the genome of both strains.
Pinedo-Rivilla
Cristina
C
Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, República Saharaui s/n, Apdo. 40, 11510 Puerto Real, Cádiz, Spain.
Aleu
Josefina
J
Grande Benito
Manuel
M
Collado
Isidro G
IG
D000935:Antifungal Agents / Q000737:chemistry* / Q000378:metabolism* / Q000494:pharmacology; D055162:Biocatalysis; D020171:Botrytis / Q000737:chemistry* / Q000187:drug effects / Q000378:metabolism*; D006868:Hydrolysis; D007189:Indans / Q000737:chemistry* / Q000378:metabolism* / Q000494:pharmacology; D008049:Lipase / Q000378:metabolism; D008968:Molecular Conformation; D013237:Stereoisomerism
D000935:Antifungal Agents; D007189:Indans; D008049:Lipase