Optimization of Synthesis of (S)-Omeprazole Catalyzed by Soybean Pod Peroxidase in Water-in-Oil Microemulsions Using RSM

Tang, Hui; Zhang, Yuanyuan; Deng, Yashan; Du, Shanshan; Li, Depeng; Wang, Zhiyong; Li, Huiling; Gao, Xin; Wang, Fanye

doi:10.1007/s10562-021-03681-x

Cited by 3 publications

(2 citation statements)

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“…386 The oxidation of omeprazole sulfide to ( S )-omeprazole was catalyzed by SBP in CTAB/isooctane/ n -butyl alcohol/water water-in-oil microemulsions. 387 A bioelectrocatalytic system was developed with CPO for oxidation of thioanisole to ( R )-methylphenylsulfoxide (Fig. 22).…”

Section: Reactions Catalyzed By Peroxidasesmentioning

confidence: 99%

Electrochemical transformations catalyzed by cytochrome P450s and peroxidases

Kumar

Rusling

2023

Chem. Soc. Rev.

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Section: Reactions Catalyzed By Peroxidasesmentioning

confidence: 99%

Electrochemical transformations catalyzed by cytochrome P450s and peroxidases

Kumar

Rusling

2023

Chem. Soc. Rev.

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“…Peroxygenases and peroxidases constitute another group of oxidative enzymes that use hydroperoxides as oxidants and display high potential in the oxyfunctionalization of organic molecules [ 26 , 27 , 28 ] without the need of cofactors, and some of them were found able to enantioselectively oxidize sulfur atom of sulfides [ 29 , 30 ] even in a non-conventional medium [ 31 , 32 , 33 ]. Among these enzymes, unspecific peroxygenases (UPOs, E.C 1.11.2.1), which are extracellular enzymes produced by many fungi, proved to be versatile catalysts in different reactions, also including the functionalization of non-activated carbons and heteroatoms [ 34 ].…”

Section: Introductionmentioning

confidence: 99%

Expanding the Use of Peroxygenase from Oat Flour in Organic Synthesis: Enantioselective Oxidation of Sulfides

Sanfilippo

Cernuto

Patti

2023

IJMS

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Biocatalyzed oxidations are an important target in sustainable synthesis since chemical oxidations often require harsh conditions and metal-based catalysts. A raw peroxygenase-containing enzymatic preparation from oat flour was tested as a biocatalyst for the enantioselective oxidation of sulfides to sulfoxides and the variations of some reaction parameters were evaluated. Under optimal conditions, thioanisole was fully converted into the corresponding (R)-sulfoxide with high optical purity (80% ee) and the same stereopreference was maintained in the oxidation of some other sulfides. Changes in the substituent on the sulfur atom affected the selectivity of the enzyme and the best results were obtained with phenyl methoxymethyl sulfide, which gave the corresponding sulfoxide in 92% ee as exclusive product. The over-oxidation of sulfides to sulfones was instead detected in all the other cases and preferential oxidation of the (S)-enantiomer of the sulfoxide intermediate was observed, albeit with low selectivity. Carrying out the oxidation of thioanisole up to the 29% formation of sulfone led to enhancement of the sulfoxide optical purity (89% ee). The activity in sulfoxidation reactions, in addition to that reported in the epoxidation of different substrates, makes this plant peroxygenase a promising and useful tool in organic synthesis.

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