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Complete stereoinversion of L-tryptophan by a fungal single module nonribosomal peptide synthetase
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Hai, Yang, Jenner, Matthew and Tang, Yi (2019) Complete stereoinversion of L-tryptophan by a fungal single module nonribosomal peptide synthetase. Journal of the American Chemical Society, 141 (41). pp. 16222-16226. doi:10.1021/jacs.9b08898
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WRAP-complete-stereoinversion-L-tryptophan-fungal-single-module-nonribosomal-peptide-syntetase-Jenner-2019.pdf - Accepted Version Embargoed item. Restricted access to Repository staff only until 1 October 2020. Contact author directly, specifying your specific needs. - Requires a PDF viewer. Download (1097Kb) |
Official URL: http://dx.doi.org/10.1021/jacs.9b08898
Abstract
Single-module nonribosomal peptide synthetases (NRPSs) and NRPS-like enzymes activate and transform carboxylic acids in both primary and secondary metabolism and are of great interest due to their biocatalytic potentials. The single-module NRPS IvoA is essential for fungal pigment biosynthesis. Here, we show that IvoA catalyzes ATP-dependent unidirectional stereoinversion of l-tryptophan to d-tryptophan with complete conversion. While the stereoinversion is catalyzed by the epimerization (E) domain, the terminal condensation (C) domain stereoselectively hydrolyzes d-tryptophanyl-S-phosphopantetheine thioester and thus represents a noncanonical C domain function. Using IvoA, we demonstrate a biocatalytic stereoinversion/deracemization route to access a variety of substituted d-tryptophan analogs in high enantiomeric excess.
| Item Type: | Journal Article | ||||||||
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| Divisions: | Faculty of Science > Chemistry | ||||||||
| Journal or Publication Title: | Journal of the American Chemical Society | ||||||||
| Publisher: | American Chemical Society | ||||||||
| ISSN: | 0002-7863 | ||||||||
| Official Date: | 16 October 2019 | ||||||||
| Dates: |
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| Date of first compliant deposit: | 11 November 2019 | ||||||||
| Volume: | 141 | ||||||||
| Number: | 41 | ||||||||
| Page Range: | pp. 16222-16226 | ||||||||
| DOI: | 10.1021/jacs.9b08898 | ||||||||
| Status: | Peer Reviewed | ||||||||
| Publication Status: | Published | ||||||||
| Publisher Statement: | This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/jacs.9b08898 | ||||||||
| Access rights to Published version: | Restricted or Subscription Access |
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