Biotransformations of steroid compounds by Chaetomium sp. KCH 6651

Janeczko, Tomasz; Dmochowska-Gładysz, Jadwiga; Kostrzewa-Susłow, Edyta; Białońska, Agata; Ciunik, Zbigniew

doi:10.1016/j.steroids.2009.02.006

Cited by 31 publications

(16 citation statements)

References 20 publications

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“…Hydroxylation at C-7 produces very useful hydroxysteroids of pharmacological value (32,33). Although many fungi have been reported to mediate 7-hydroxylation of steroids (34)(35)(36)(37)(38)(39)(40)(41)(42), low stereoselectivity (7␣/7␤) (38,41) and side hydroxylation reactions (37,42) have often been observed, thus presenting great challenges in developing highly regio-and stereoselective 7-hydroxylation processes of steroidal compounds.…”

Section: Discussionmentioning

confidence: 99%

Distinct Regioselectivity of Fungal P450 Enzymes for Steroidal Hydroxylation

Lü

Feng

Chen

et al. 2019

Appl Environ Microbiol

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In this study, we identified two P450 enzymes (CYP5150AP3 and CYP5150AN1) from Thanatephorus cucumeris NBRC 6298 by combination of transcriptome sequencing and heterologous expression in Pichia pastoris. The biotransformation of 11-deoxycortisol and testosterone by Pichia pastoris whole cells coexpressing the cyp5150ap3 and por genes demonstrated that the CYP5150AP3 enzyme possessed steroidal 7β-hydroxylase activities toward these substrates, and the regioselectivity was dependent on the structures of steroidal compounds. CYP5150AN1 catalyzed the 2β-hydroxylation of 11-deoxycortisol. It is interesting that they display different regioselectivity of hydroxylation from that of their isoenzyme, CYP5150AP2, which possesses 19- and 11β-hydroxylase activities. IMPORTANCE The steroidal hydroxylases CYP5150AP3 and CYP5150AN1 together with the previously characterized CYP5150AP2 belong to the CYP5150A family of P450 enzymes with high amino acid sequence identity, but they showed completely different regioselectivities toward 11-deoxycortisol, suggesting the regioselectivity diversity of steroidal hydroxylases of CYP5150 family. They are also distinct from the known bacterial and fungal steroidal hydroxylases in substrate specificity and regioselectivity. Biocatalytic hydroxylation is one of the important transformations for the functionalization of steroid nucleus rings but remains a very challenging task in organic synthesis. These hydroxylases are useful additions to the toolbox of hydroxylase enzymes for the functionalization of steroids at various positions.

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Section: Discussionmentioning

confidence: 99%

Distinct Regioselectivity of Fungal P450 Enzymes for Steroidal Hydroxylation

Lü

Feng

Chen

et al. 2019

Appl Environ Microbiol

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“…Products 93 (14%) and 94 (75%) were isolated from the biotransformation of 11 using Chaetomium sp. (Figure 13) [73].…”

Section: Microbiological Transformations Of Steroidsmentioning

confidence: 99%

“…were 93 (21%), 94 (39%), and 99 (19%); after 24 h of incubation, the presence of 11 was detected. Janeczko et al [73] concluded that the steric factors associated with the substrate determine the location and orientation of the hydroxyl group. For example, the carbonyl group in C-17 at 11 directs the entry of the hydroxyl group at C-14 with α orientation, while the hydroxylation in C-6β is favored by the presence of the hydroxyl group in C-17, as in 12.…”

Section: Microbiological Transformations Of Steroidsmentioning

confidence: 99%

“…For example, the carbonyl group in C-17 at 11 directs the entry of the hydroxyl group at C-14 with α orientation, while the hydroxylation in C-6β is favored by the presence of the hydroxyl group in C-17, as in 12. In the case of progesterone (1), which has an acyl group, dihydroxylated derivatives were observed in C-6 and C-14 ( Figure 15) [73].…”

Section: Microbiological Transformations Of Steroidsmentioning

confidence: 99%

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Biotransformation of Steroids Using Different Microorganisms

Cano-Flores¹,

Gómez²,

Ramos³

2020

Chemistry and Biological Activity of Steroids

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The introduction of a hydroxyl group "biohydroxylation" in the steroid skeleton is an important step in the synthesis of new steroids used physiologically as hormones and active drugs. There are currently about 300 known steroid drugs whose production constitutes the second category within the pharmaceutical market after antibiotics. Several biotransformations at industrial scale have been applied in the production of steroid hormones and drugs, which have functionalized different types of raw materials by means of chemo-, regio-, and stereoselective reactions (hydroxylation, Baeyer-Villiger oxidation, oxidation reactions, reduction of group carbonyl, isomerization, and Michael additions, condensation reactions, among others). In Green Chemistry, biotransformations are an important chemical methodology toward more sustainable industrial processes.

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“…In many cases, hydroxy derivatives are characterized with much higher biological activity than the less polar substrate (Janeczko et al, 2009;Donova and Egorova, 2012). For example, 11α-HP is one of the main steps in the production of corticosteroid hormones (corticosterone, cortisone and hydrocortisone) (Hanisch et al, 1980;Znidarsic et al, 2000).…”

Section: Introductionmentioning

confidence: 99%

Biotransformation of progesterone to hydroxysteroid derivatives by whole cells of Mucor racemosus

Mohamed¹,

El-Refai²,

Sallam³

et al. 2013

MJM

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Aims:The possibility of using Mucor racemosus cells in the biotransformation of progesterone to industrially important hydroxysteroid derivatives in one-step biotransformation process was investigated in this study Methodology and results: The fungal strain was inoculated into the transformation medium which supplemented with PR as a substrate (5-50 mg). The transformation products were separated and characterized on the bases of their GC/MS analysis as 11α-hydroxyprogesterone (11α-HP) as main product (I); 4-pregnen-18-al-11β,21-diol-3,20-dione (Aldosterone) (II) and 20-hydroxy-pregnan-18-oic acid (III) as minor products. The organism was tested for PR bioconversion at different transformation periods (6-96 h), as well as optimization of the basal medium through the addition of different concentrations of yeast extract and peptone (0.5 to 4 g/L) at various pH values (4-9). The optimal biotransformation conditions for maximum production of these PR derivatives were observed using 0.2 g/L of PR, 3 g/L of yeast extract and 3 g/L peptone after 48 h at pH value 5.5. Under these optimal conditions, cells total bioconversion efficiency reached about 96% of the original added PR. Conclusion, significance and impact of study: Under these optimum conditions, M. racemosus has the ability to biotransform PR to 11α-HP (I), Aldosterone (II) and 20-hydroxy-pregnan-18-oic acid (III) with total bioconversion efficiency of 96 ± 1.77%. These results may be of industrial importance because compounds II and III had not been previously recorded as biotransformation products of PR.

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Biotransformations of steroid compounds by Chaetomium sp. KCH 6651

Cited by 31 publications

References 20 publications

Distinct Regioselectivity of Fungal P450 Enzymes for Steroidal Hydroxylation

Distinct Regioselectivity of Fungal P450 Enzymes for Steroidal Hydroxylation

Biotransformation of Steroids Using Different Microorganisms

Biotransformation of progesterone to hydroxysteroid derivatives by whole cells of Mucor racemosus

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