Highly regio- and stereoselective hydroxylation of vitamin D2 by CYP109E1

Putkaradze, Natalia; König, Lisa; Kattner, Lars; Hutter, Michael C.; Bernhardt, Rita

doi:10.1016/j.bbrc.2020.01.091

Cited by 12 publications

(15 citation statements)

References 22 publications

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“…[ 59 , 60 ] Wild‐type CYP109E1 has been identified to highly regio‐ and stereoselectively hydroxylate vitamin D2 via two‐step dihydroxylation (Figure 7 ). [59] …”

Section: Oxyfunctionalisation: Nature's Manifold Ways Of Forming C−o Bondsmentioning

confidence: 99%

“…[57,58] Moreover,r ecent examples report on the dihydroxylation of either two aliphatic or aromatic CÀHb onds within av itamin D2 motif and benzene derivatives,r espectively. [59,60] Wild-type CYP109E1 has been identified to highly regio-and stereoselectively hydroxylate vitamin D2 via two-step dihydroxylation (Figure 7). [59] Additionally,P450s have been engineered towards multiple oxyfunctionalisations.…”

Section: Hydroxylationmentioning

confidence: 99%

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Enzymatic Late‐Stage Modifications: Better Late Than Never

et al. 2021

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Enzyme catalysis is gaining increasing importance in synthetic chemistry. Nowadays, the growing number of biocatalysts accessible by means of bioinformatics and enzyme engineering opens up an immense variety of selective reactions. Biocatalysis especially provides excellent opportunities for late‐stage modification often superior to conventional de novo synthesis. Enzymes have proven to be useful for direct introduction of functional groups into complex scaffolds, as well as for rapid diversification of compound libraries. Particularly important and highly topical are enzyme‐catalysed oxyfunctionalisations, halogenations, methylations, reductions, and amide bond formations due to the high prevalence of these motifs in pharmaceuticals. This Review gives an overview of the strengths and limitations of enzymatic late‐stage modifications using native and engineered enzymes in synthesis while focusing on important examples in drug development.

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“…[ 59 , 60 ] Wild‐type CYP109E1 has been identified to highly regio‐ and stereoselectively hydroxylate vitamin D2 via two‐step dihydroxylation (Figure 7 ). [59] …”

Section: Oxyfunctionalisation: Nature's Manifold Ways Of Forming C−o Bondsmentioning

confidence: 99%

Section: Hydroxylationmentioning

confidence: 99%

Enzymatic Late‐Stage Modifications: Better Late Than Never

et al. 2021

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“…Arens: [59,60] Wildtyp-CYP109E1 hydroxyliert Vitamin D2 hochgradig regio-und stereoselektiv in einer Zwei-Schritt-Dihydroxylierung (Abbildung 7). [59] Darüber hinaus wurden P450-Enzyme im Hinblick auf multiple Oxyfunktionalisierungen konstruiert. [60,61] Eine Dreifachmutante von CYP154E1 bewerkstelligte die konsekutive oxidative N-Demethylierung sowie regio-und stereoselektive C6-Hydroxylierung.…”

Section: Hydroxylierungunclassified

“…Das Wildtypenzym P450 TxtC ermçglicht aliphatische sowie aromatische C-H-Hydroxylierungeni nd er späten Funktionalisierung eines Diketopiperazins (18). [57,58] Zudem berichten aktuelle Beispiele über die Dihydroxylierung zweier aliphatischer oder aromatischer C-H-Bindungen innerhalb eines Vitamin-D2-Motivs bzw.A rens: [59,60] Wildtyp-CYP109E1 hydroxyliert Vitamin D2 hochgradig regio-und stereoselektiv in einer Zwei-Schritt-Dihydroxylierung (Abbildung 7). [59] Darüber hinaus wurden P450-Enzyme im Hinblick auf multiple Oxyfunktionalisierungen konstruiert.…”

Section: Hydroxylierungunclassified

“…[57,58] Zudem berichten aktuelle Beispiele über die Dihydroxylierung zweier aliphatischer oder aromatischer C-H-Bindungen innerhalb eines Vitamin-D2-Motivs bzw.A rens: [59,60] Wildtyp-CYP109E1 hydroxyliert Vitamin D2 hochgradig regio-und stereoselektiv in einer Zwei-Schritt-Dihydroxylierung (Abbildung 7). [59] Darüber hinaus wurden P450-Enzyme im Hinblick auf multiple Oxyfunktionalisierungen konstruiert. [60,61] Eine Dreifachmutante von CYP154E1 bewerkstelligte die konsekutive oxidative N-Demethylierung sowie regio-und stereoselektive C6-Hydroxylierung.D amit konnte das Antidepressivum (2S,6S)-Hydroxynorketamin (20)a us (S)-Ketamin erhalten werden.…”

Section: Hydroxylierungunclassified

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Enzymkatalysierte späte Modifizierungen: Besser spät als nie

Romero

Jones²,

Hogg³

et al. 2021

Angewandte Chemie

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Microbial P450 repertoire (P450ome) and its application feasibility in pharmaceutical industry, chemical industry, and environmental protection

Wang,

Pan,

Wang

et al. 2023

Biotech & Bioengineering

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Cytochrome P450s (CYPs) are heme‐thiolated enzymes that catalyze the oxidation of C‐H bonds in a regio‐ and stereo‐selective manner. CYPs are widely present in the biological world. With the completion of more biological genome sequencing, the number and types of P450 enzymes have increased rapidly. P450 in microorganisms is easy to clone and express, rich in catalytic types, and strong in substrate adaptability, which has good application potential. Although the number of P450 enzymes found in microorganisms is huge, the function of most of the microorganism P450s has not been studied, and it contains a large number of excellent biocatalysts to be developed. This review is based on the P450 groups in microorganisms. First, it reviews the distribution of P450 groups in different microbial species, and then studies the application of microbial P450 enzymes in the pharmaceutical industry, chemical industry and environmental pollutant treatment in recent years. And focused on the application fields of P450 enzymes of different families to guide the selection of suitable P450s from the huge P450 library. In view of the current shortcomings of microbial P450 in the application process, the final solution is the most likely to assist the application of P450 enzymes in large‐scale, that is, whole cell transformation combined with engineering, fusion P450 combined with immobilization technology.

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Highly regio- and stereoselective hydroxylation of vitamin D2 by CYP109E1

Cited by 12 publications

References 22 publications

Enzymatic Late‐Stage Modifications: Better Late Than Never

Enzymatic Late‐Stage Modifications: Better Late Than Never

Enzymkatalysierte späte Modifizierungen: Besser spät als nie

Microbial P450 repertoire (P450ome) and its application feasibility in pharmaceutical industry, chemical industry, and environmental protection

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