Enzymatic one-step ring contraction for quinolone biosynthesis

The 6,6-quinolone scaffolds on which viridicatin-type fungal alkaloids are built are frequently found in metabolites that display useful biological activities. Here we report in vitro and computational analyses leading to the discovery of a hemocyanin-like protein AsqI from the Aspergillus nidulans...

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Autores principales: Kishimoto, Shinji, Hara, Kodai, Hashimoto, Hiroshi, Hirayama, Yuichiro, Champagne, Pier Alexandre, Houk, Kendall N., Tang, Yi, Watanabe, Kenji
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2018
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6053404/
https://www.ncbi.nlm.nih.gov/pubmed/30026518
http://dx.doi.org/10.1038/s41467-018-05221-5
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author Kishimoto, Shinji
Hara, Kodai
Hashimoto, Hiroshi
Hirayama, Yuichiro
Champagne, Pier Alexandre
Houk, Kendall N.
Tang, Yi
Watanabe, Kenji
author_facet Kishimoto, Shinji
Hara, Kodai
Hashimoto, Hiroshi
Hirayama, Yuichiro
Champagne, Pier Alexandre
Houk, Kendall N.
Tang, Yi
Watanabe, Kenji
author_sort Kishimoto, Shinji
collection PubMed
description The 6,6-quinolone scaffolds on which viridicatin-type fungal alkaloids are built are frequently found in metabolites that display useful biological activities. Here we report in vitro and computational analyses leading to the discovery of a hemocyanin-like protein AsqI from the Aspergillus nidulans aspoquinolone biosynthetic pathway that forms viridicatins via a conversion of the cyclopenin-type 6,7-bicyclic system into the viridicatin-type 6,6-bicyclic core through elimination of carbon dioxide and methylamine through methyl isocyanate.
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spelling pubmed-60534042018-07-25 Enzymatic one-step ring contraction for quinolone biosynthesis Kishimoto, Shinji Hara, Kodai Hashimoto, Hiroshi Hirayama, Yuichiro Champagne, Pier Alexandre Houk, Kendall N. Tang, Yi Watanabe, Kenji Nat Commun Article The 6,6-quinolone scaffolds on which viridicatin-type fungal alkaloids are built are frequently found in metabolites that display useful biological activities. Here we report in vitro and computational analyses leading to the discovery of a hemocyanin-like protein AsqI from the Aspergillus nidulans aspoquinolone biosynthetic pathway that forms viridicatins via a conversion of the cyclopenin-type 6,7-bicyclic system into the viridicatin-type 6,6-bicyclic core through elimination of carbon dioxide and methylamine through methyl isocyanate. Nature Publishing Group UK 2018-07-19 /pmc/articles/PMC6053404/ /pubmed/30026518 http://dx.doi.org/10.1038/s41467-018-05221-5 Text en © The Author(s) 2018 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Kishimoto, Shinji
Hara, Kodai
Hashimoto, Hiroshi
Hirayama, Yuichiro
Champagne, Pier Alexandre
Houk, Kendall N.
Tang, Yi
Watanabe, Kenji
Enzymatic one-step ring contraction for quinolone biosynthesis
title Enzymatic one-step ring contraction for quinolone biosynthesis
title_full Enzymatic one-step ring contraction for quinolone biosynthesis
title_fullStr Enzymatic one-step ring contraction for quinolone biosynthesis
title_full_unstemmed Enzymatic one-step ring contraction for quinolone biosynthesis
title_short Enzymatic one-step ring contraction for quinolone biosynthesis
title_sort enzymatic one-step ring contraction for quinolone biosynthesis
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6053404/
https://www.ncbi.nlm.nih.gov/pubmed/30026518
http://dx.doi.org/10.1038/s41467-018-05221-5
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