Monoamine Oxidase (MAO-N) Whole Cell Biocatalyzed Aromatization of 1,2,5,6-Tetrahydropyridines into Pyridines

Toscani, Anita; Risi, Caterina; Black, Gary W.; Brown, Nicola L.; Shaaban, Ali; Turner, Nicholas J.; Castagnolo, Daniele

doi:10.1021/acscatal.8b02386

Cited by 31 publications

(21 citation statements)

References 35 publications

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“…As a natural evolution of this work, MAO-N biocatalysts were then used for the synthesis of pyridine derivatives 103 from 1,2,5,6-tetrahydropyridine substrates 101 (Scheme 22, b). 40 As a result, the MAO-N D9 variant proved to be the best biocatalyst for this biotransformation. It was hypothesized that the aromatization proceeds through an initial C-N bond oxidation catalyzed by MAO-N, which leads to the formation of intermediates 102, followed by a second spontaneous oxidation by air.…”

Section: Scheme 21 Chemo-enzymatic Synthesis Of Pyridines Using Laccamentioning

confidence: 95%

Biocatalytic and Chemo-Enzymatic Approaches for the Synthesis of Heterocycles

Zhao¹,

Masci²,

Tomarelli³

et al. 2020

Synthesis

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Heterocycles are ubiquitous structures in nature and can be found in many drugs and chemicals. Biocatalysts, alone or in combination with other metal catalysts, can be exploited for the construction of various heterocyclic rings under mild reaction conditions. This Short Review highlights the recent advances in the development of biocatalytic and chemo-enzymatic methods for the synthesis of both aliphatic and aromatic heterocyclic rings.1 Introduction2 Synthesis of Aliphatic Heterocycles2.1 Piperidines, Pyrrolidines and Piperazines2.2 Other Nitrogen-Containing Aliphatic Heterocycles2.3 Lactones and Lactams2.4 Other Oxygen-Containing Heterocycles3 Synthesis of Aromatic Heterocycles3.1 Pyrroles, Pyridines and Pyrazines3.2 Furans3.3 Bicyclic Aromatic Heterocycles4 Conclusion

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Section: Scheme 21 Chemo-enzymatic Synthesis Of Pyridines Using Laccamentioning

confidence: 95%

Biocatalytic and Chemo-Enzymatic Approaches for the Synthesis of Heterocycles

Zhao¹,

Masci²,

Tomarelli³

et al. 2020

Synthesis

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“…[230] Rowbotham et al demonstrated an elegant approach for the asymmetric reductive deuteration by NADH reductases using H 2 as the reductant along with 2 H 2 Oa sa ni sotope source.H ydrogenase and NAD + reductase were co-immobilised on carbon particles, enabling the resultant H 2 -driven system to reduce NAD + to [4-2 H]-NADH. Coupling with aKRED facilitated deuterium transfer onto ketone 240,t hus affording al abelled alcohol (241). [231] 6.2.…”

Section: = Oreductionmentioning

confidence: 99%

“…[239] MAO-N variants have also been used in ad ifferent context, to generate both pyrroles and pyridines from appropriate dihydro-and tetrahydro-precursors. [240,241] Extensive engineering of MAO-N proved useful in desymmetrisation of API building blocks leading to enantiomerically pure amine precursors. [242] Thel ate-stage amination towards the antidiabetic drug sitagliptin (259)r epresents an outstanding example achieved by Codexis and Merck (Scheme 44).…”

Section: = Oreductionmentioning

confidence: 99%

“… [239] MAO‐N variants have also been used in a different context, to generate both pyrroles and pyridines from appropriate dihydro‐ and tetrahydro‐precursors. [ 240 , 241 ] Extensive engineering of MAO‐N proved useful in desymmetrisation of API building blocks leading to enantiomerically pure amine precursors. [242] …”

Section: Reduction Of Double Bondsmentioning

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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“…[239] MAO-N-Varianten wurden außerdem verwendet, um Pyrrole sowie Pyridine aus den entsprechenden Dihydro-und Te trahydro-Vorstufen zu generieren. [240,241] Ausgiebiges Engineering der MAO-N erwies sich als nützlich in der Desymmetrisierung von Wirkstoff-Bausteinen, um enantiomerenreine Amin-Vorstufen zu bilden. [242] Der Antidiabetes-Wirkstoff Sitagliptin (259)s piegelt ein ausgezeichnetes Beispiel fürdie späte Aminierung durch eine von Codexis und Merck entwickelte Tr ansaminase wider (Schema 44).…”

Section: Angewandte Chemieunclassified