Strategies to Produce Chlorinated Indole‐3‐Acetic Acid and Indole‐3‐Acetic Acid Intermediates. Issue 34 (4th December 2017)

• Record Type: Journal Article
• Authors: Patallo, Eugenio P.; Walter, Antje; Milbredt, Daniela; Thomas, Marion; Neumann, Madeleine; Caputi, Lorenzo; O'Connor, Sarah; Ludwig‐Müller, Jutta; van Pée, Karl‐Heinz
• Is Part Of: ChemistrySelect. Volume 2:Issue 34(2017)
• Page Start: 11148
• Page End: 11153
• Publication Date: 2017-12-04
• Subjects: chloroindole acetic acid -- chloroindole acetonitrile -- chlorotryptophan -- halogenase -- indole acetic acid; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201701933
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: Tryptophan and indole derivatives are common precursors in many natural biosynthetic pathways. In recent years it has been shown that the substrate specificity of tryptophan halogenases is much more relaxed than previously thought. Using the tryptophan 7‐halogenase PrnA, the tryptophan 6‐halogenase ThdH, and the tryptophan 5‐halogenase PyrH we achieved the regioselective mono‐halogenation of indole‐3‐acetic acid (IAA), which has not been reported as a substrate of tryptophan halogenases to date. The tryptophan 5‐halogenase gene was introduced into Arabidopsis thaliana leading to the formation of 5‐chlorotryptophan, 5‐chloroindole‐3‐acetonitrile and 5‐chloro‐3‐indole acetic acid by A. thaliana . PyrH activity could also be demonstrated for the plant‐produced halogenase in vitro . These results show the potential of flavin‐dependent halogenases to generate novel halogenated auxins or other secondary metabolites in vitro and in vivo by plants. Abstract : Transformation of Arabidopsis thaliana with the tryptophan 5‐halogenase gene pyrH leads to formation of 5‐chlorotryptophan which is converted to 5‐chloroindole‐3‐acetic acid via 5‐chloroindole‐3‐acetonitrile. 5‐Chloroindole‐3‐acetic acid can also be formed in vitro by direct chlorination of indole‐3‐acetic acid by PyrH.