Abstract Since ancient times, people have been attracted by dyes and they were a symbol of power. Some of the oldest dyes are indigo and its derivative Tyrian purple, which were extracted from plants and snails, respectively. These ‘indigoid dyes’ were and still are used for coloration of textiles and as a food additive. Traditional Chinese medicine also knows indigoid dyes as pharmacologically active compounds and several studies support their effects. Further, they are interesting for future technologies like organic electronics. In these cases, especially the indigo derivatives are of interest but unfortunately hardly accessible by chemical synthesis. In recent decades, more and more enzymes have been discovered that are able to produce these indigoid dyes and therefore have gained attention from the scientific community. In this study, group E monooxygenases (styrene monooxygenase and indole monooxygenase) were used for the selective oxygenation of indole (derivatives). It was possible for the first time to show that the product of the enzymatic reaction is an epoxide. Further, we synthesized and extracted indigoid dyes and could show that there is only minor by-product formation (e.g. indirubin or isoindigo). Thus, group E monooxygenase can be an alternative biocatalyst for the biosynthesis of indigoid dyes.

中文翻译：

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E组单加氧酶的靛类染料：机制和生物催化

摘要 自古以来，人们就被染料所吸引，染料是权力的象征。一些最古老的染料是靛蓝及其衍生物 Tyrian 紫，它们分别从植物和蜗牛中提取。这些“靛蓝染料”过去和现在仍然用于纺织品着色和作为食品添加剂。中医也知道靛蓝染料是具有药理活性的化合物，并且有几项研究支持它们的作用。此外，它们对有机电子等未来技术很有趣。在这些情况下，尤其是靛蓝衍生物是令人感兴趣的，但遗憾的是很难通过化学合成获得。近几十年来，越来越多的酶被发现能够产生这些靛蓝染料，因此受到了科学界的关注。在这项研究中，E组单加氧酶（苯乙烯单加氧酶和吲哚单加氧酶）用于吲哚（衍生物）的选择性氧化。首次证明酶促反应的产物是环氧化物成为可能。此外，我们合成并提取了靛蓝染料，可以证明只有少量副产物形成（例如靛玉红或异靛蓝）。因此，E 组单加氧酶可以作为生物合成靛蓝染料的替代生物催化剂。