97724-36-2Relevant articles and documents
A tunable synthesis of indigoids: Targeting indirubin through temperature
Cheek, Joshua T.,Horner, John S.,Kaller, Kaylie S.,Kinsey, Ally L.,Shriver, James A.,Sterrenberg, Summer R.,Van Vors, Madison K.,Wang, Katelyn R.
, p. 5407 - 5414 (2022/03/01)
The spontaneous conversion of 3-indoxyl to indigo is a well-established process used to produce indigo dyes. It was recently shown that some indoles, when reacted with molybdenum hexacarbonyl and cumyl peroxide, proceed through an indoxyl intermediate to produce significant amounts of indirubin through a competing mechanism. Modulation of this system to lower temperatures allows for careful tuning, leading to selective production of indirubins in a general process. A systematic assay of indoles show that electron deficient indoles work well when substituted at the 5 and 7 positions. In contrast, 6-substituted electron rich indoles give the best results whereas halogeno indoles work well in all cases. This process shows broad functional group tolerance for generally reactive carbonyl-containing compounds such as aldehydes and carboxylic acids. This journal is
Indigoid dyes by group e monooxygenases: Mechanism and biocatalysis
Heine, Thomas,Gro?mann, Carolin,Hofmann, Sarah,Tischler, Dirk
, p. 939 - 950 (2019/03/19)
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.
Exploring the biocatalytic scope of a bacterial flavin-containing monooxygenase
Rioz-Martinez, Ana,Kopacz, Malgorzata,De Gonzalo, Gonzalo,Torres Pazmino, Daniel E.,Gotor, Vicente,Fraaije, Marco W.
experimental part, p. 1337 - 1341 (2011/04/23)
A bacterial flavin-containing monooxygenase (FMO), fused to phosphite dehydrogenase, has been used to explore its biocatalytic potential. The bifunctional biocatalyst could be expressed in high amounts in Escherichia coli and was able to oxidize indole and indole derivatives into a variety of indigo compounds. The monooxygenase also performs the sulfoxidation of a wide range of prochiral sulfides, showing moderate to good enantioselectivities in forming chiral sulfoxides. The Royal Society of Chemistry 2011.
