Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
18302 | Enzyme and Microbial Technology | 2007 | 8 Pages |
Mannich base derivatives 1–3 were biotransformed through tandem enzymatic reactions by using several microorganisms isolated from Brazilian biomes. The hydrochlorides 1 and 3 produced propiophenone 1a, α,β-unsatured ketone 2c and alcohol (S)-1b (yield 40%, e.e. 81%, Aspergillus terreus). The hydrochloride 2 underwent the Baeyer–Villiger oxidation producing exclusively para-methoxy-phenol by A. terreus and A. niger. The propiophenone 1a was reduced to their corresponding enantiomerically enriched phenylpropanol (S)-1b (yield 65%, e.e. 81%, A. terreus). The para-methoxy-propiophenone 2a afforded Baeyer–Villiger reaction hydrolyzed product, the para-methoxy-phenol (yield 80%, A. terreus). The racemic phenylpropanols 1b,2b were resolved by lipase-catalyzed kinetic resolution (Novozym 435) affording (S)-alcohols 1b,2b and (R)-acetates 1d,2d in high enantiomeric excesses (up to 99%) and good yields (40–45%). We screened new microorganisms in biotransformation of Mannich bases, propiophenones and applied enzymatic resolution of phenylpropanols by Candida antarctica lipase.