Microbial Baeyer–Villiger oxidation of 5α-steroids using Beauveria bassiana. A stereochemical requirement for the 11α-hydroxylation and the lactonization pathway

Świzdor, Alina; Panek, Anna; Milecka-Tronina, Natalia

doi:10.1016/j.steroids.2014.01.006

Cited by 27 publications

(20 citation statements)

References 33 publications

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“…[9] For many years, our team has conducted research on microbial functionalization of compounds of natural origin, including steroid systems. [10][11][12][13][14][15][16][17][18][19][20] Among these transformations, the hydroxylation reactions in an inactivated position of a transformed compound are of particular importance. The use of biotransformation as a tool for modification of the molecules makes it possible to obtain derivatives that are found in the nature in minor amounts, as well as new analogues in amounts which not only allow for determination of their structure, but also for biological assays.…”

Section: Biohydroxylation Of 7-oxo-dhea a Natural Metabolite Of Dheamentioning

confidence: 99%

“…7-Oxo-DHEA (307 mg, 42% yield) was found to be in excess of 99.1% purity following GC and elemental analysis, anal. C 75.49, H 8.72%, calcd for C 19…”

Section: -En-717-dione (7-oxo-dhea) (1)mentioning

confidence: 99%

“…Amorphous solid; C 19 (CH, C-14), 45.0 (CH, C-14), 43.5 (C, C-13), 41.8 (CH 2 , C-4), 38.4 (C, C-10), 36.2 (CH 2 , C-1), 35.5 (CH 2 , C-12), 31.2 (CH 2 , C-2), 30.9 (CH 2 , C-16), 25.7 (CH 2 , C-15), 21.0 (CH 2 , C-11), 17.4 (CH 3 , C-19), 11.0 (CH 3 , C-18).…”

Section: β3β-dihydroxy-androst-5-en-717-dione (2)mentioning

confidence: 99%

“…For many years, our team has conducted research on microbial functionalization of compounds of natural origin, including steroid systems . Among these transformations, the hydroxylation reactions in an inactivated position of a transformed compound are of particular importance.…”

mentioning

confidence: 99%

“…, 3.61 (1H, dd, J = 11.4 Hz, 4.4 Hz, H-1α), 3.70-3.76 (1H, m, H-3α), 5.85 (1H, br s, H-6); 13 C NMR (CDCl 3 , 75 MHz) δ 220.5 (C, C-17), 200.9 (C, C-7), 162.8 (CH, C-5), 128.1 (CH, C-6), 75.9 (CH, C-1), 66.3 (CH, C-3), 50.2 (CH, C-9), 47.4 (C, C-13), 45.5 (CH, C-8), 44.8 (CH, C-14), 44.5 (C, C-10), 42.2 (CH 2 , C-2), 41.7 (CH 2 , C-4), 35.5 (CH 2 , C-16), 30.9 (CH 2 , C-12), 24.2 (CH 2 , C-15), 23.1 (CH 2 , C-11), 13.8 (CH 3 , C-18), 11.7 (CH 3 , C-19).3β,12β-Dihydroxy-androst-5-en-7,17-dione (3)Amorphous solid; C19 H 26 O 4 : calcd. C, 71.67; H, 8.23; found.…”

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confidence: 99%

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Biohydroxylation of 7‐oxo‐DHEA, a natural metabolite of DHEA, resulting in formation of new metabolites of potential pharmaceutical interest

2016

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Metabolism of steroids in healthy and unhealthy human organs is the subject of extensive clinical and biomedical studies. For this kind of investigations, it is essential that the reference samples of new derivatives of natural, physiologically active steroids (especially those difficult to achieve in the chemical synthesis) become available. This study demonstrated for the first time transformation of 7-oxo-DHEA-a natural metabolite of DHEA, using Syncephalastrum racemosum cells. The single-pulse fermentation of substrate produced two new hydroxy metabolites: 1β,3β-dihydroxy-androst-5-en-7,17-dione and 3β,12β-dihydroxy-androst-5-en-7,17-dione, along with the earlier reported 3β,9α-dihydroxy-androst-5-en-7,17-dione and 3β,17β-dihydroxy-androst-5-en-7-one. Simultaneously, the same metabolites, together with small quantities of 7α- and 7β-hydroxy-DHEA, as well as the products of their reduction at the C-17 were obtained after transformation of DHEA under pulse-feeding of the substrate. The observed reactions suggested that this micro-organism contains enzymes exhibiting similar activity to those present in human cells. Thus, the resulting compounds can be considered as potential components of the eukaryotic, including human, metabolome.

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Section: Biohydroxylation Of 7-oxo-dhea a Natural Metabolite Of Dheamentioning

confidence: 99%

“…7-Oxo-DHEA (307 mg, 42% yield) was found to be in excess of 99.1% purity following GC and elemental analysis, anal. C 75.49, H 8.72%, calcd for C 19…”

Section: -En-717-dione (7-oxo-dhea) (1)mentioning

confidence: 99%

Section: β3β-dihydroxy-androst-5-en-717-dione (2)mentioning

confidence: 99%

mentioning

confidence: 99%

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confidence: 99%

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Biohydroxylation of 7‐oxo‐DHEA, a natural metabolite of DHEA, resulting in formation of new metabolites of potential pharmaceutical interest

2016

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Regioselective Baeyer–Villiger Oxidation of Steroidal Ketones to Lactones Using BF₃/H₂O₂

et al. 2020

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Chemical Synthesis of Rare Natural Bile Acids: 11α‐Hydroxy Derivatives of Lithocholic and Chenodeoxycholic Acids

Namegawa

Iida

Omura

et al. 2018

Lipids

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A method for the preparation of 11α-hydroxy derivatives of lithocholic and chenodeoxycholic acids, recently discovered to be natural bile acids, is described. The principal reactions involved were (1) elimination of the 12α-mesyloxy group of the methyl esters of 3α-acetate-12α-mesylate and 3α,7α-diacetate-12α-mesylate derivatives of deoxycholic acid and cholic acid with potassium acetate/hexamethylphosphoramide; (2) simultaneous reduction/hydrolysis of the resulting △ -3α-acetoxy and △ -3α,7α-diacetoxy methyl esters with lithium aluminum hydride; (3) stereoselective 11α-hydroxylation of the △ -3α,24-diol and △ -3α,7α,24-triol intermediates with B H /tetrahydrofuran (THF); and (4) selective oxidation at C-24 of the resulting 3α,11α,24-triol and 3α,7α,11α,24-tetrol to the corresponding C-24 carboxylic acids with NaClO catalyzed by 2,2,6,6-tetramethylpiperidine 1-oxyl free radical (TEMPO) and NaClO. In summary, 3α,11α-dihydroxy-5β-cholan-24-oic acid and 3α,7α,11α-trihydroxy-5β-cholan-24-oic acid have been synthesized and their nuclear magnetic resonance (NMR) spectra characterized. These compounds are now available as reference standards to be used in biliary bile acid analysis.

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Microbial Baeyer–Villiger oxidation of 5α-steroids using Beauveria bassiana. A stereochemical requirement for the 11α-hydroxylation and the lactonization pathway

Cited by 27 publications

References 33 publications

Biohydroxylation of 7‐oxo‐DHEA, a natural metabolite of DHEA, resulting in formation of new metabolites of potential pharmaceutical interest

Biohydroxylation of 7‐oxo‐DHEA, a natural metabolite of DHEA, resulting in formation of new metabolites of potential pharmaceutical interest

Regioselective Baeyer–Villiger Oxidation of Steroidal Ketones to Lactones Using BF₃/H₂O₂

Chemical Synthesis of Rare Natural Bile Acids: 11α‐Hydroxy Derivatives of Lithocholic and Chenodeoxycholic Acids

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Microbial Baeyer–Villiger oxidation of 5α-steroids using Beauveria bassiana. A stereochemical requirement for the 11α-hydroxylation and the lactonization pathway

Cited by 27 publications

References 33 publications

Biohydroxylation of 7‐oxo‐DHEA, a natural metabolite of DHEA, resulting in formation of new metabolites of potential pharmaceutical interest

Biohydroxylation of 7‐oxo‐DHEA, a natural metabolite of DHEA, resulting in formation of new metabolites of potential pharmaceutical interest

Regioselective Baeyer–Villiger Oxidation of Steroidal Ketones to Lactones Using BF3/H2O2

Chemical Synthesis of Rare Natural Bile Acids: 11α‐Hydroxy Derivatives of Lithocholic and Chenodeoxycholic Acids

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Regioselective Baeyer–Villiger Oxidation of Steroidal Ketones to Lactones Using BF₃/H₂O₂