Oxidation of organoselenium compounds. A study of chemoselectivity of phenylacetone monooxygenase

Andrade, Leandro H.; Pedrozo, Eliane C.; Leite, Henrique G.; Brondani, Patrícia Bulegon

doi:10.1016/j.molcatb.2011.07.018

Cited by 14 publications

(6 citation statements)

References 32 publications

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“…Similarly to peroxides, BVMOs were early found to promiscuously catalyze heteroatom oxidations as well. , Sulfoxidations are particularly well studied and many enzymes produced sulfoxides with high enantioselectivity. ,− Several existing patents describing the use of BVMOs for selective sulfoxidations emphasize the commercial potential. − Other reactions include oxidations of amines, ,,, boron, ,, and selenium. ,, A single report of phosphite ester and iodine oxidation yet awaits further exploration, as do the few reports of epoxidations catalyzed by BVMOs. , An entirely different approach to induce promiscuous catalytic activity is the use of BVMOs under anaerobic conditions to prevent peroxyflavin formation. Recent results with AcCHMO suggest that the so-stabilized reduced flavin can catalyze reductions, allowing tunable, stereoselective ketoreductase-like reactions …”

Section: Promiscuous Catalytic Activitiesmentioning

confidence: 99%

“…12 6 − 1 2 8 Other reactions include oxidations of amines, 40,102,129,130 boron, 98,131,132 and selenium. 98,133,134 A single report of phosphite ester and iodine oxidation yet awaits further exploration, 98 as do the few reports of epoxidations catalyzed by BVMOs. 135,136 An entirely different approach to induce promiscuous catalytic activity is the use of BVMOs under anaerobic conditions to prevent peroxyflavin formation.…”

Section: ■ Promiscuous Catalytic Activitiesmentioning

confidence: 99%

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Baeyer–Villiger Monooxygenases: Tunable Oxidative Biocatalysts

et al. 2019

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Pollution, accidents, and misinformation have earned the pharmaceutical and chemical industry a poor public reputation, despite their undisputable importance to society. Biotechnological advances hold the promise to enable a future of drastically reduced environmental impact and rigorously more efficient production routes at the same time. This is exemplified in the Baeyer–Villiger reaction, which offers a simple synthetic route to oxidize ketones to esters, but application is hampered by the requirement of hazardous and dangerous reagents. As an attractive alternative, flavin-containing Baeyer–Villiger monooxygenases (BVMOs) have been investigated for their potential as biocatalysts for a long time, and many variants have been characterized. After a general look at the state of biotechnology, we here summarize the literature on biochemical characterizations, mechanistic and structural investigations, as well as enzyme engineering efforts in BVMOs. With a focus on recent developments, we critically outline the advances toward tuning these enzymes suitable for industrial applications.

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Section: Promiscuous Catalytic Activitiesmentioning

confidence: 99%

Section: ■ Promiscuous Catalytic Activitiesmentioning

confidence: 99%

Baeyer–Villiger Monooxygenases: Tunable Oxidative Biocatalysts

et al. 2019

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“…In addition to sulfide, other heteroatoms such as nitrogen, − boron, − and selenium compounds − can also be oxygenated, but they are less investigated compared to the enantioselective sulfoxidations. Some representative cases are displayed here, such as CHMO Acineto catalyzed asymmetric oxidations of secondary and tertiary amines to the corresponding amine N-oxides (Scheme a and b). , Moreover, class B flavin-dependent monooxygenases Aspergillus fumigatus siderophore (SidA), a N-hydroxylating monooxygenase (NMO), can catalyze the hydroxylation of the side-chain amino group and also stimulate a lot of mechanism studies (Scheme c) …”

Section: Homogeneous Oxygenase-catalyzed Oxygenationsmentioning

confidence: 99%

Homogeneous Oxygenase Catalysis

et al. 2018

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Oxygenases-catalyzed reductive activation of molecular oxygen and incorporation of O atoms into an organic molecule is undoubtedly one of the most attractive research areas. Typically, these oxygenation reactions proceed with high selectivity and reactivity, which is seldom found in its "biomimetic" chemocatalytic counterparts. Furthermore, enzymatic oxygenation can avoid undesired overoxidation, which is frequently observed in (industrial) chemical transformation. Therefore, it is not surprising that tremendous attention has been paid to enzymatic oxygenation. Their application in organic synthesis has been steadily growing over the years. The goal of the present Review is to provide a handy reference for chemists interested in using homogeneous oxygenase catalysis and those interested in discovering new types of biomimetic oxidations and oxygenations with dioxygen. In this Review, we will review the recent advances in in homogeneous oxygenase catalysis to reveal the great achievements and potentials in this field.

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“…Less complex cyclic or arylic ketones were also oxidised by Beauveria (Fuganti et al, 1998;Osorio-Lozada et al, 2008)), Cunninghamella (Alphand et al, 1998), Curvularia (Ouazzani-Chahdi et al, 1987Goncalvez et al, 2004), Drechslera (Goncalvez et al, 2004), Dipodascus (Fujii et al, 2007); Exophiala (Hasegawa et al, 2000), Fusarium (Kawamoto et al, 2008), Gibberella (Fraga et al, 2009), Geotrichum (Carballeira et al, 2004), Emericella and Aspergillus strains (Andrade et al, 2011;Fill et al, 2012;Keppler et al, 2005). Some of these biotransformations were optimised for synthetic purposes (Fujii et al, 2007;Mazzini et al, 1997aMazzini et al, , 1997b.…”

Section: Selection Of Fungimentioning

confidence: 99%