Show simple item record

dc.contributor.authorMcClay, K.
dc.contributor.authorMehboob, S.
dc.contributor.authorYu, J.
dc.contributor.authorSantarsiero, BD
dc.contributor.authorDeng, J.
dc.contributor.authorCook, JL
dc.contributor.authorJeong, J.
dc.contributor.authorJohnson, ME
dc.contributor.authorSteffan, RJ
dc.date.accessioned2016-01-27T17:13:18Z
dc.date.available2016-01-27T17:13:18Z
dc.date.issued2015
dc.identifier.bibliographicCitationMcClay, K., Mehboob, S., Yu, J., Santarsiero, B. D., Deng, J. P., Cook, J. L., Jeong, H., Johnson, M. E. and Steffan, R. J. Indole trimers with antibacterial activity against Gram-positive organisms produced using combinatorial biocatalysis. AMB Express. 2015. 5. DOI: 10.1186/s13568-015-0125-4.en_US
dc.identifier.issn2191-0855
dc.identifier.urihttp://hdl.handle.net/10027/20053
dc.descriptionThis is the copy of an article published in the AMB Express © 2015 Springer Open Publications. © 2015 McClay et al. © The Author(s).en_US
dc.description.abstractThe I100V isoform of toluene-4-monooxygenase was used to catalyze the oxidative polymerization of anthranil and various indoles under mildly acidic conditions, favoring the production of trimers. Compounds produced in sufficient yield were purified and tested for their ability to inhibit the growth of B. anthracis, E. faecalis, L. monocytogenes, S. aureus, and in some cases, F. tularensis. 15 of the compounds displayed promising antibacterial activity (MIC < 5 µg/ml) against one or more of the strains tested, with the best MIC values being <0.8 µg/ml. All of these compounds had good selectivity, showing minimal cytotoxicity towards HepG2 cells. The structure was solved for six of the compounds that could be crystallized, revealing that minimally two classes of indole based trimers were produced. One compound class produced was a group of substituted derivatives of the natural product 2,2-bis(3-indolyl) indoxyl. The other group of compounds identified was classified as tryptanthrin-like compounds, all having multi-ring pendant groups attached at position 11 of tryptanthrin. One compound of particular interest, SAB-J85, had a structure that suggests that any compound, with a ring structure that can be activated by an oxygenase, might serve as a substrate for combinatorial biocatalysis.en_US
dc.publisherSpringerOpenen_US
dc.titleIndole trimers with antibacterial activity against Gram-positive organisms produced using combinatorial biocatalysis.en_US
dc.typeArticleen_US


Files in this item

Thumbnail

This item appears in the following Collection(s)

Show simple item record