甲苯双加氧酶催化苯并[b]噻吩和苯并[b]呋喃的顺式二羟基化反应：苯并[b]噻吩 2,3-氧化物的合成。
Toluene dioxygenase-catalyzed cis-dihydroxylation of benzo[b]thiophenes and benzo[b]furans: synthesis of benzo[b]thiophene 2,3-oxide.
机构信息
School of Chemistry and Chemical Engineering, Queens University, Belfast, N Ireland.
出版信息
Org Biomol Chem. 2012 Sep 28;10(36):7292-304. doi: 10.1039/c2ob26120k.
Enzymatic cis-dihydroxylation of benzo[b]thiophene, benzo[b]furan and several methyl substituted derivatives was found to occur in both the carbocyclic and heterocyclic rings. Relative and absolute configurations and enantiopurities of the resulting dihydrodiols were determined. Hydrogenation of the alkene bond in carbocyclic cis-dihydrodiols and ring-opening epimerization/reduction reactions of heterocyclic cis/trans-dihydrodiols were also studied. The relatively stable heterocyclic dihydrodiols of benzo[b]thiophene and benzo[b]furan showed a strong preference for the trans configuration in aqueous solutions. The 2,3-dihydrodiol metabolite of benzo[b]thiophene was utilized as a precursor in the chemoenzymatic synthesis of the unstable arene oxide, benzo[b]thiophene 2,3-oxide.
苯并[b]噻吩、苯并[b]呋喃和几种甲基取代衍生物的酶促顺式二羟基化反应被发现同时发生在碳环和杂环中。确定了所得二氢二醇的相对和绝对构型和对映纯度。还研究了碳环顺式二氢二醇中烯烃键的加氢和杂环顺/反式二氢二醇的开环差向异构化/还原反应。苯并[b]噻吩和苯并[b]呋喃的相对稳定的杂环二氢二醇在水溶液中强烈倾向于反式构型。苯并[b]噻吩的 2,3-二氢二醇代谢物被用作不稳定的芳烃氧化物苯并[b]噻吩 2,3-氧化物的化学酶促合成前体。
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