Stereoselective bioreduction of β-carboline imines through cell-free extracts from earthworms (Eisenia foetida)

Mirabal‐Gallardo, Yaneris; Soriano, Manuel; Santos, Leonardo S.

doi:10.1016/j.tetasy.2013.03.003

Cited by 17 publications

(6 citation statements)

References 57 publications

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“…In a follow‐up study, the same research group has investigated the reduction of dihydro‐β‐carbolines 54 by a rather extraordinary biocatalyst – a crude cell‐free extract of the Californian earthworm, Eisenia foetida (Scheme , D) 63 . E. foetida extracts formed the desired tetrahydro‐β‐carbolines 55 in decent yields (63–80%) and with excellent enantioselectivities ( ee between 92% and >99%).…”

Section: Imine Reduction Employing Wild‐type Microbial Cellsmentioning

confidence: 99%

Biocatalytic Imine Reduction and Reductive Amination of Ketones

2015

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Chiral aminesr epresent ap rominentf unctional group in pharmaceuticals and agrochemicals and are hence attractive targets for asymmetric synthesis.S ince the pharmaceutical industry has identified biocatalysis as av aluablet oolf or synthesising chiral molecules with high enantiomeric excess and under mild reactionc onditions,e nzymatic methods for chiral amine synthesisa re increasing in importance.A mong the strategies available in this context, the asymmetric reductiono fi mines by NAD(P)Hdependent enzymes andt he related reductive amination of ketones have long remained underrepresented. However, recent years have witnessed an impressive progress in the applicationo fn atural or engineered imine-reducing enzymes,s uch as imine reductases,o pine dehydrogenases,a mine dehydrogenases, and artificial metalloenzymes.T his review provides ac omprehensive overview of biocatalytic imine reductiona nd reductive amination of ketones,h ighlightingt he natural roles,s ubstrate scopes,s tructural features, and potential applicationf ields of the involvedenzymes.1I ntroduction 2I mine Reduction in Nature 2. 1I ntroductionChiral amines represent the core structure of am yriad of natural products as well as man-made compounds of public demand, such as pharmaceuticals and agrochemicals (Figure 1). Accordingt o recent estimates,c hiral amine moieties are present in about 40% of active pharmaceutical ingredients (APIs) and 20% of agrochemicals.[1] Moreover, optically pure amines,a mino acids,a nd amino alcohols are frequently employed in chemical synthesis as chiral auxiliariesorr esolving agents.Theirp aramount importance across several chemical disciplines andi ndustrial sectors has made chiral amines anda mino acids attractive targets for asymmetrics ynthesis.E stablished approachesf or their preparation are the stereoselective addition of nucleophiles to imines (including the famous Mannich and Strecker reactions), asymmetric C À Ha mination and hydroamination, and the asymmetric reductiono fe namines and imines,w hich may either be pre-formed or may occur as intermediates in an asymmetric reductive amination process.[2] Metallo-or organocatalytic methodsf or asymmetric imine and enamine reductiona re broadly applied, and intense research efforts are devoted to the improvement of the scope and stereoselectivity of these processes. [2,3] In cases where established asymmetric synthesism ethodsa re inapplicable or fail to provide the desired optical purity, diastereomeric salt crystallisation is still widely used for the classical resolution of racemic amines or for upgrading the enantiomeric excess of an optically enriched product.[2d]Biocatalytic transformationsa re increasingly being recognised as an attractive optionf or the asymmetric synthesiso fc hiral molecules.[4] Particularly in the

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Section: Imine Reduction Employing Wild‐type Microbial Cellsmentioning

confidence: 99%

Biocatalytic Imine Reduction and Reductive Amination of Ketones

2015

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“…There is an increase in the search by enantiomerically pure compounds, that are of great interest to pharmaceutical and agrochemistry industry, it has boosted research in biocatalysis area (Labes and Wendhausen, 2008;Gallardo et al, 2013) 1,5-bis-(2-methoxy-phenyl)-penta-3-ol (3a): δ 1.75 (m, 4H, H-2/H-4), 2.80 (m, 4H, H-1/H-5), δ 3.75 (quint, 1H, H-3), 7.23-7.33 (m, 10H, H-Ar), 3,85 (s, 6H, OMe-7/OMe-7').…”

Section: Resultsmentioning

confidence: 99%

Bioreduction of α,β-unsaturated carbonyl compounds by Lasiodiplodia pseudotheobromae, endophytic fungus from Morinda citrifolia (RUBIACEAE)

Silva

Anjos

Oliveira

et al. 2020

RSD

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Biotransformations are reactions carried out by microorganisms that lead to changes in the structures of organic compounds, among the biotransformations there are bioreductions. Bioreductions are of great interest to the pharmaceutical and food industries, as they almost always lead to the formation of enantiomerically pure compounds. Thus, this work aimed to verify the ability of the fungus Lasiodiplodia pseudotheobromae in bioreduce α,β-unsaturated carbonyl compounds. Compounds (3E)-4-(2-methoxy-phenyl)-but-3-en-2-one (1), (1E, 4E)-1,5-diphenyl-pent-1,4-dien-3-one (2) and (1E, 4E)-1,5-bis-(2-methoxy-phenyl)-penta-1,4-dien-3-one (3) were used as substrates. The reactions were carried out on an orbital shaker for 8 days at room temperature. The products formed were characterized by analytical thin layer chromatography (ATLC), high performance liquid chromatography (HPLC) and hydrogen nuclear magnetic resonance (1H NMR). For all products formed was observed reduction in double bonds C=C and C=O leading to the formation of the respective alcohols. This is the first report of biotransformation reactions using the fungus Lasiodiplodia pseudotheobromae.

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“…Scheme 27 ). 118 Several non-natural tetrahydro-β-carbolines were also synthesised in these studies in 45–83% yield and 50% to >99% enantiomeric excess.…”

Section: Biocatalytic Reduction Of Imines and Iminium Ionsmentioning

confidence: 98%