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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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Official URL: http://dx.doi.org/10.1021/jacs.9b08898

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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
Subjects: Q Science > QP Physiology
T Technology > TP Chemical technology
Divisions: Faculty of Science > Chemistry
Library of Congress Subject Headings (LCSH): Enzymes, Peptides, Tryptophan, Fungi -- Biotechnology
Journal or Publication Title: Journal of the American Chemical Society
Publisher: American Chemical Society
ISSN: 0002-7863
Official Date: 16 October 2019
Dates:
DateEvent
16 October 2019Published
1 October 2019Available
1 October 2019Accepted
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
RIOXX Funder/Project Grant:
Project/Grant IDRIOXX Funder NameFunder ID
1R35GM118056National Institutes of Healthhttp://dx.doi.org/10.13039/100000002
Life Sciences Research Foundation FellowshipMark Foundation For Cancer Researchhttp://dx.doi.org/10.13039/100014599
BB/R01212/1[BBSRC] Biotechnology and Biological Sciences Research Councilhttp://dx.doi.org/10.13039/501100000268
BB/M017982/1[BBSRC] Biotechnology and Biological Sciences Research Councilhttp://dx.doi.org/10.13039/501100000268

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