Biotransformation of (S)-cis-verbenol with Nocardia corallina B-276

Abstract

A biotransformação de (S)-cis-verbenol com Nocardia corallina foi investigada usando-se dois procedimentos: Suspensão de células em tampão de fosfatos (pH 7), com várias relações substrato: células e bioreator de 3-L com células em meio de cultura. (1S)-(-)-verbenona foi obtida com excelentes rendimentos que variaram de >99% a 98%, em escala de 0,7 e 7 mmol respectivamente. The biotransformation of (S)-cis-verbenol with Nocardia corallina was investigated using two methods: Suspension of cells in a phosphate buffer (pH 7) with various substrate:cells ratios; and bioreactor of 3-L with cells in the culture media. Both gave (1S)-(-)-verbenone with excellent yields ranging from >99 to 98%, at scale of 0.7 and 7 mmol respectively.

Application of the redox system of Nocardia corallina B-276 in the enantioselective biotransformation of ketones and alcohols

“…The sample was centrifuged at 4500 rpm for 15 min and then extracted with ethyl acetate (3×15 mL), and the organic layer was concentrated to dryness. 15 The products 1a or 1b were identified by FT--IR and NMR and the spectra were in full accordance with literature. 20,21 The product was dissolved in 0.5 mL of HPLC 2-propanol and analyzed by GC using a Supelcowax™-10 column (30m×0.25mm, 0.25 µm) at 180 °C with N 2 as carrier gas at 0.8 mL min -1 , the retention times were t R (1a) = 4.39 min and t R (1b) = 5.63 min.…”

“…12 Nocardia corallina B-276 (ATCC 31338) is a versatile microorganism that catalyzes redox processes, such as the oxidation of aldehydes, allylic and benzylic alcohols to obtain carboxylic acids or ketones, and enantioselective reduction of ketones to secondary alcohols in an ecofriendly manner, with good yields. [13][14][15][16][17] The aim of this research was to evaluate the redox system of Nocardia corallina B-276 in the biotransformation of 1-phenyl-1-propanone (1a), 2-hydroxy-1-phenylethanone (2a), methyl (2-chlorophenyl)(oxo)acetate (3a), 1-phen-BIOTRANSFORMATION OF KETONES AND ALCOHOLS 281 ylpropan-1-ol (1b), 1-phenyl-1,2-ethanediol (2b) and methyl (2-chlorophenyl)-(hydroxy)acetate (3b) ( Fig. 1).…”

Microbial Oxidation of (-)-α-pinene to Verbenol Production by Newly Isolated Strains

“…The use of biotransformation has significant advantages over chemical reactions and in the last 10 years has been increasing constantly since biocatalysts have attracted much attention from the viewpoint of green chemistry [1].…”

Optimization of α-Terpineol Production by the Biotransformation of R-(+)-Limonene and (−)-β-Pinene

“…Toniazzo et al [18] tested Aspergillus niger and A. niger ATCC 9642 in the limonene biotransformation and achieved a conversion in α-terpineol of 0.68%±0.19 and 0.13%±0.07, respectively. Maróstica Junior and Pastore [10] investigated the microorganisms Penicillium sp. 2025, Aspergillus sp.…”

“…This fact can be considered true due to the advantages of the biotransformation process compared to chemical synthesis, besides the high potential offered by the microbial transformation in producing new compounds of flavor with different applications in industries, but biotechnological improvements to enhance the production are indispensable [10,11].…”