Biotransformation of acetophenone to 1-phenylethanol by fungi

Abstract

The fungi Botrytis cinerea and Colletotrichum acutatum were used to convert acetophenone to 1-phenylethanol. B. cinerea produced a 98.5% yield of 1-phenylethanol with an enantiomeric excess of 93.8%. Conversely, addition of 1-phenylethanol did not change the reaction rate or product composition. In contrast, the reaction catalyzed by C. acutatum was markedly slower, commencing only after an approximately three-day delay. The concentration of substrate decreased gradually over approximately 14 days, coinciding with increased production of 1-phenylethanol. Phenol was produced after 18 days, and the final yields of 1-phenylethanol and phenol were 38.1% and 61.5%, respectively.

Biotransformation of 4-Chromanone, 4-Flavanone, and their Analogs by Fungi

“…In addition, a recent study used the protein secretome of B. cinerea for biotransformation reactions, such as that of resveratrol [17]. Here we report the biotransformation of 4-chromanone and its analogs as a follow-up to our study using acetophenones [10] 2. EXPERIMENTAL…”

“…We hypothesize that this reaction involves biocatalysts, such as oxidoreductase, which require NAPDH as a coenzyme. The reaction mechanism was discussed in detail in our previous publication [10]. Table 1.…”

“…Recently, we reported the biotransformation of acetophenone using two fungi, Botrytis cinerea and Colletotrichum acutatum, as biocatalysts [10]. Although we used two types of phytopathogenic fungi, other studies have reported using B. cinerea and Colletotrichum spp.…”

Biotransformation of 4-Chromanol, 4-Flavanol, Xanthydrol, and their Analogs by Tissue Cultured Cells

“…For callus induction of C. maxima and P. neapolitanum, tissues were obtained by surface sterilization of young shoots and leaves for 10 s in 70% ethanol and 5 min in 1% sodium hydrochloride. The tissues were washed three times with sterile distilled water and transferred onto agar MS medium supplemented with 3% sucrose, 2.1 mg/L 2,4-dichlorophenoxy acetic acid (2,4-D), and 0.2 mg/mL kinetin [17,18]. After successive subculturing, the cell-suspensions were cultured in 100 mL of liquid MS medium on an orbital shaker at 70 rpm at 24 • C in the dark.…”

“…Furthermore, the Hamada group at the Okayama University of Science has investigated organic synthesis methods using tissue culture cells of higher plants as biocatalysts for reactions such as the glycosylation of terpenes [12][13][14][15][16]. We previously showed that biotransformations using mold could reduce carbonyl compounds to their alcohol form [17,18]. Conversely, cells in plant tissue cultures produced the reverse reaction; that is, the oxidation of the alcohol derivative to its carboxylic acid, such as geraniol to geranoic acid (geranic acid) [19].…”