Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, República Saharaui s/n, Apdo. 40, 11510 Puerto Real, Cádiz, Spain.
Org Biomol Chem. 2010 Aug 21;8(16):3784-9. doi: 10.1039/c003938a. Epub 2010 Jun 23.
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.
使用生物催化方法制备了对映体纯的 2-苯并茚衍生物，并确定了它们的绝对构型。（1R,2S）-2-苯并茚-1-醇（（1R,2S）-2）和（S）-2-苯并茚-1-酮（（S）-3）是通过发酵面包酵母产生的。脂肪酶介导的相应外消旋底物的酯化和水解产生了对映体纯的化合物（1S,2R）-2-苯并茚-1-醇（（1S,2R）-2）和（1R,2S）-2-苯并茚-1-醇（（1R,2S）-2）。测试了这些产物对两种植物病原菌 Botrytis cinerea 的抗真菌活性。还描述了 B. cinerea 作为真菌解毒机制的一部分对抗-（±）-2-苯并茚-1-醇（抗-（±）-2）的代谢，并揭示了两种菌株基因组的有趣差异。
