Recent Advances in the Synthesis of 19‐Norsteroids

Windholz, T. B.; Windholz, Martha

doi:10.1002/anie.196403531

Cited by 24 publications

(7 citation statements)

References 62 publications

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“…Among the various hydroxylation reactions of steroids, hydroxylation at C-19 produces a very useful hydroxysteroid intermediate for the synthesis of 19-nor-steroids without the C-19 angular methyl group in three chemoenzymatic steps (see, for example, 19-nor-androstenedione in Fig. 1), while they are currently prepared in a series of 10 chemical reactions (8). The 19-nor-steroids are widely used key intermediates for the production of highly effective contraceptives, such as norethindrone (9), mifepristone (10), and tibolone (11).…”

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confidence: 99%

A Fungal P450 Enzyme from Thanatephorus cucumeris with Steroid Hydroxylation Capabilities

Lü

Chen

Feng

et al. 2018

Appl Environ Microbiol

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In this study, we identified a P450 enzyme (STH10) and an oxidoreductase (POR) from NBRC 6298 by a combination of transcriptome sequencing and heterologous expression in The biotransformation of 11-deoxycortisol was performed by using the whole cells co-expressing and , and the product analysis indicated that the STH10 enzyme possessed steroidal 19- and 11β-hydroxylase activities. This is a novel fungal P450 enzyme with 19-hydroxylase activity, which is different from the known steroidal aromatase CYP19 and CYP11B families of enzymes. Hydroxylation is one of the most important reactions in steroid functionalization, especially C19-hydroxylation produces a key intermediate for the synthesis of 19-nor-steroid drugs without C19 angular methyl group in three chemo-enzymatic steps, instead of the current industrial process with ten chemical reactions. However, hydroxylation of the C19 angular methyl group remains a very challenging task due to the large steric resistance to the 19 methyl group between the A and B rings. The present study reports a novel fungal P450 enzyme with 19-hydroxylase activity. This opens a new venue for searching effective biocatalysts for the useful steroidal C-19 hydroxylation, although further studies for better understanding of the structural basis underlying regioselectivity and substrate specificity of this fungal steroidal 19-hydroxylase is warranted to facilitate the engineering of this enzyme for the industrial applications.

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confidence: 99%

A Fungal P450 Enzyme from Thanatephorus cucumeris with Steroid Hydroxylation Capabilities

Lü

Chen

Feng

et al. 2018

Appl Environ Microbiol

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“…[74][75] o C (lit. [13] 78-79 o C), with spectroscopic data (IR, NMR, MS) identical with those of authentic plumbagin.…”

Section: Isolation Of Plumbaginmentioning

confidence: 67%

“…Having done this successfully, we then embarked on the isolation of some natural quinones, namely plumbagin, morindone, and erythrolaccin, from the roots of Plumbago rosea, Morinda angustifolia and from seedlac, respectively. Plumbagin (5-hydroxy-2-methyl-1,4-naphthoquinone) is a well-known natural naphthoquinone [13], while morindone (1,2,5-trihydroxy-6-methylanthraquinone) is a less well-known isomer of emodin, useful as a red dye for cotton [14]. Erythrolaccin (1,3,5,6-tetrahydroxy-8-methylanthraquinone) is a yellow dyestuff present in seedlac obtained from crude lac, a resinous substance secreted by the scale insect Laccifer lacca [15a].…”

Section: Resultsmentioning

confidence: 99%

Electrocoagulation of Quinone Pigments

et al. 2006

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Some representative quinones, viz. one naphthoquinone (plumbagin) and five anthraquinones (alizarin, purpurin, chrysazin, emodin, and anthrarufin), were subjected to electrocoagulation. It was found that the rate and extent of coagulation of these compounds appears to correlate with the number and relative position of their phenolic substituent groups, and that all of the coagulated quinones could be recovered. Attempts were then made to electrochemically isolate three quinones, namely plumbagin, morindone and erythrolaccin, from natural sources.

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“…An improved synthesis emerged, in which both compounds were obtained, while the aromatisation and Birch reduction could be avoided. [41,42] As starting point serves 5-androsten-3β-ol-17-one acetate, to which hypochlorous acid is added. Notable is the thermal or photochemical functionalisation of C-19 with lead tetraacetate/iodine, [43] under formation of a cyclic ether.…”

Section: Oestrone 19-nortestosteronementioning

confidence: 99%