15α-Hydroxylation of a steroid (13-ethyl-gon-4-en-3,17-dione) by Penicillium raistrickii in an ionic liquid/aqueous biphasic system

Abstract

Biphasic processes are used in whole-cell biotransformation to overcome the low water solubility of substrates and products as well as their inhibitory effects on the biocatalyst. Commercially available [NTf(2)]- and [PF(6)]-based ionic liquids (ILs) were used in a biphasic system for the 15α-hydroxylation of 13-ethyl-gon-4-en-3,17-dione by Penicillium raistrickii. With the substrate at 5 g l(-1) and a volume ratio of IL to buffer, buffer pH and cell density at, 1:9, 6.5, 16.8 g(DW) l(-1), respectively, the 15α-hydroxylation of 13-ethyl-gon-4-en-3,17-dione was achieved with a yield of 70 % after 72 h using [BMIm][NTf(2)] in a 50 ml biphasic system. This is compared to a 30 % yield in a monophasic aqueous system. This suggests the potential industrial application of ILs-based biphasic systems for steroid biotransformation.

Side-chain cleavage of phytosterols byMycobacteriumsp. MB 3683 in a biphasic ionic liquid/aqueous system

“…Figure also shows that IL with [PF 6 ]‐anion achieved slightly higher production than that with [NTf 2 ]‐anion for phytosterols biotransformation in the presence of the same cation of [BMIM]. Nevertheless, the results may depend strongly on distinct biocatalysts and reactions in actual process …”

“…Water‐immiscible ILs can be good alternatives to organic solvents to construct biphasic systems having the advantages of tunable physical and chemical properties, no vapor pressure at room temperature and non‐flammability . So far the few studies of IL–aqueous biphasic systems used in steroids bioconversion have mainly focused on steroids hydroxylation; few reports have been published concerning the influence of ILs on sterols side‐chain degradation processes. The only report was conducted by Marques et al , who applied four ILs to construct single IL phase systems or 1:1 IL:aqueous biphasic systems for the selective cleavage of the side‐chain of β‐sitosterol performed by free resting cells of Mycobacterium sp.…”

Synergistic effects of components in deep eutectic solvents relieve toxicity and improve the performance of steroid biotransformation catalyzed by Arthrobacter simplex

“…The metabolic activity retention (MAR) as measured by sugar conversion can be used as a proxy for the biocompatibility of DESs as well as for the metabolic activity of A. simplex . As shown in Fig.…”

“…19,20 The effect of the DESs and their components on glucose uptake The metabolic activity retention (MAR) as measured by sugar conversion can be used as a proxy for the biocompatibility of DESs as well as for the metabolic activity of A. simplex. [32][33][34][35][36] As shown wileyonlinelibrary.com/jctb in Fig. 1, the MAR value varied greatly in the three DES-containing systems when 6% of the DESs was used, among which ChCl: Gly (DES) exhibited the best metabolic activity with the highest MAR value of 43.90%.…”

Efficient hydroxylation of functionalized steroids by Colletotrichum lini ST-1

“…The oxygen group in position C11 was regarded as essential for anti-inflammatory action [36]. Also 15␣-hydroxylations were important reactions in the production of gestodene, which was a progestogen with oral contraceptive properties [37]. Comparison of the transformation results between 3-keto-steroids of (3-7) (Figs.…”