Microbiological transformation of steroids. I. Synthesis of 19-nortestololactone

McCurdy, Judith T.; Garrett, Ronald D.

doi:10.1021/jo01266a039

Cited by 7 publications

(2 citation statements)

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“…Therefore we have included representatives of 19-OH steroids in our biotransformation experiments. Biosynthetic routes from 19-nortestosterone to 19-nortestololactone were established with the use of biocatalytic fungi Aspergillus tamarii [ 23 ] and Penicillium notatum [ 24 ], but we were able to obtain in the current study better final yields than those presented in the earlier reports.…”

Section: Introductionmentioning

confidence: 66%

“…In the presented studies, in the course of a six-day biotransformation 19-nortestololactone ( 13 ) was obtained with good yield of 90%. An established biosynthetic route to 19-nortestololactone utilizes 72 h transformation of 19-nortestosterone by Aspergillus tamarii with 70% yield (16 × 50 mg/500 mL) [ 23 ]. In another known example of transformation of 19-nortestosterone by Penicillium notatum , 19-nortestololactone was obtained with 93% yield, but at lower substrate concentration (100 mg/300 mL medium) [ 24 ] than in the current report.…”

Section: Resultsmentioning

confidence: 99%

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Microbial Modifications of Androstane and Androstene Steroids by Penicillium vinaceum

2020

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The biotransformation of steroid compounds is a promising, environmentally friendly route to new pharmaceuticals and hormones. One of the reaction types common in the metabolic fate of steroids is Baeyer-Villiger oxidation, which in the case of cyclic ketones, such as steroids, leads to lactones. Fungal enzymes catalyzing this reaction, Baeyer-Villiger monooxygenases (BVMOs), have been shown to possess broad substrate scope, selectivity, and catalytic performance competitive to chemical oxidation, being far more environmentally green. This study covers the biotransformation of a series of androstane steroids (epiandrosterone and androsterone) and androstene steroids (progesterone, pregnenolone, dehydroepiandrosterone, androstenedione, 19-OH-androstenedione, testosterone, and 19-nortestosterone) by the cultures of filamentous fungus Penicillium vinaceum AM110. The transformation was monitored by GC and the resulting products were identified on the basis of chromatographic and spectral data. The investigated fungus carries out effective Baeyer-Villiger oxidation of the substrates. Interestingly, introduction of the 19-OH group into androstenedione skeleton has significant inhibitory effect on the BVMO activity, as the 10-day transformation leaves half of the 19-OH-androstenedione unreacted. The metabolic fate of epiandrosterone and androsterone, the only 5α-saturated substrates among the investigated compounds, is more complicated. The transformation of these two substrates combined with time course monitoring revealed that each substrate is converted into three products, corresponding to oxidation at C-3 and C-17, with different time profiles and yields.

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Section: Introductionmentioning

confidence: 66%

Section: Resultsmentioning

confidence: 99%