Biocatalytic preparation and absolute configuration of enantiomerically pure fungistatic anti-2-benzylindane derivatives. Study of the detoxification mechanism by Botrytis cinerea

• Published in: Organic & biomolecular chemistry Vol. 8; no. 16; pp. 3784 - 3789
• Main Authors: Pinedo-Rivilla, Cristina, Aleu, Josefina, Grande Benito, Manuel, Collado, Isidro G
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 21.08.2010
• Subjects: Antifungal Agents - chemistry; Antifungal Agents - metabolism; Antifungal Agents - pharmacology; Biocatalysis; Botrytis - chemistry; Botrytis - drug effects; Botrytis - metabolism; Botrytis cinerea; Chemistry; Chemistry, Organic; Hydrolysis; Indans - chemistry; Indans - metabolism; Indans - pharmacology; Lipase - metabolism; Molecular Conformation; Physical Sciences; Saccharomyces cerevisiae; Science & Technology; Stereoisomerism; TRANSFORMATION; OPTICALLY-ACTIVE AMINES; KETONES; CIRCULAR-DICHROISM; REDUCTION; ENANTIOSELECTIVITY; STEREOCHEMICAL CONTROL; SECTOR; BAKERS-YEAST; PATHOGENS
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/c003938a

Enantiomerically pure 2-benzylindane derivatives were prepared using biocatalytic methods and their absolute configuration determined. (1 R ,2 S )-2-Benzylindan-1-ol ((1 R ,2 S )- 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 (1 S ,2 R )-2-benzylindan-1-ol ((1 S ,2 R )- 2 ) and (1 R ,2 S )-2-benzylindan-1-ol ((1 R ,2 S )- 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. Enantiomerically pure 2-benzylindane derivatives were prepared using biocatalytic methods and their absolute configuration determined. The antifungal activity of these products against the phytopathogen Botrytis cinerea was tested.