Aleksandra Rudzka, Tamara Reiter, Wolfgang Kroutil, P. Borowiecki
{"title":"使用乙酸乙烯酯作为乙醛代用品,ADH 催化(杂)芳香族仲醇与酮的生物氧化反应","authors":"Aleksandra Rudzka, Tamara Reiter, Wolfgang Kroutil, P. Borowiecki","doi":"10.1002/cctc.202400803","DOIUrl":null,"url":null,"abstract":"The oxidation of sec‐alcohols is a common reaction in organic chemistry. We report a biocatalytic approach for oxidizing racemic (hetero)aromatic sec‐alcohols to the corresponding ketones. The reaction relies on employing freeze‐dried E. coli cells containing a recombinant variant of an alcohol dehydrogenase deduced from Lactobacillus kefir (E. coli/Lk‐ADH Prince) and vinyl acetate as an in situ acetaldehyde surrogate as oxidant. Biooxidations of a set of 20 racemic (hetero)aromatic alcohols were carried out in the presence of a catalytic amount of NADP+ cofactor, the biocatalyst, and vinyl acetate in an aqueous medium to generate the corresponding ketones with up to >99% conv. Preparative scale (1.0 mmol; 100 mM in 10 mL) reactions led to obtaining ketones in the 56−83% isolated yield range.","PeriodicalId":503942,"journal":{"name":"ChemCatChem","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2024-06-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"ADH‐Catalyzed Biooxidation of (Hetero)aromatic sec‐Alcohols to Ketones Employing Vinyl Acetate as Acetaldehyde Surrogate\",\"authors\":\"Aleksandra Rudzka, Tamara Reiter, Wolfgang Kroutil, P. Borowiecki\",\"doi\":\"10.1002/cctc.202400803\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"The oxidation of sec‐alcohols is a common reaction in organic chemistry. We report a biocatalytic approach for oxidizing racemic (hetero)aromatic sec‐alcohols to the corresponding ketones. The reaction relies on employing freeze‐dried E. coli cells containing a recombinant variant of an alcohol dehydrogenase deduced from Lactobacillus kefir (E. coli/Lk‐ADH Prince) and vinyl acetate as an in situ acetaldehyde surrogate as oxidant. Biooxidations of a set of 20 racemic (hetero)aromatic alcohols were carried out in the presence of a catalytic amount of NADP+ cofactor, the biocatalyst, and vinyl acetate in an aqueous medium to generate the corresponding ketones with up to >99% conv. Preparative scale (1.0 mmol; 100 mM in 10 mL) reactions led to obtaining ketones in the 56−83% isolated yield range.\",\"PeriodicalId\":503942,\"journal\":{\"name\":\"ChemCatChem\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-06-06\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"ChemCatChem\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1002/cctc.202400803\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"ChemCatChem","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1002/cctc.202400803","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
ADH‐Catalyzed Biooxidation of (Hetero)aromatic sec‐Alcohols to Ketones Employing Vinyl Acetate as Acetaldehyde Surrogate
The oxidation of sec‐alcohols is a common reaction in organic chemistry. We report a biocatalytic approach for oxidizing racemic (hetero)aromatic sec‐alcohols to the corresponding ketones. The reaction relies on employing freeze‐dried E. coli cells containing a recombinant variant of an alcohol dehydrogenase deduced from Lactobacillus kefir (E. coli/Lk‐ADH Prince) and vinyl acetate as an in situ acetaldehyde surrogate as oxidant. Biooxidations of a set of 20 racemic (hetero)aromatic alcohols were carried out in the presence of a catalytic amount of NADP+ cofactor, the biocatalyst, and vinyl acetate in an aqueous medium to generate the corresponding ketones with up to >99% conv. Preparative scale (1.0 mmol; 100 mM in 10 mL) reactions led to obtaining ketones in the 56−83% isolated yield range.