Structural determinants of reductive terpene cyclization in iridoid biosynthesis

The carbon skeleton of ecologically and pharmacologically important iridoid monoterpenes is formed in a reductive cyclization reaction unrelated to canonical terpene cyclization. Here we report the crystal structure of the recently discovered iridoid cyclase (Catharanthus roseus) bound to a mechanis...

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Autores principales: Kries, Hajo, Caputi, Lorenzo, Stevenson, Clare E. M., Kamileen, Mohammed O., Sherden, Nathaniel H., Geu-Flores, Fernando, Lawson, David M., O’Connor, Sarah E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: 2015
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4685742/
https://www.ncbi.nlm.nih.gov/pubmed/26551396
http://dx.doi.org/10.1038/nchembio.1955
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author Kries, Hajo
Caputi, Lorenzo
Stevenson, Clare E. M.
Kamileen, Mohammed O.
Sherden, Nathaniel H.
Geu-Flores, Fernando
Lawson, David M.
O’Connor, Sarah E.
author_facet Kries, Hajo
Caputi, Lorenzo
Stevenson, Clare E. M.
Kamileen, Mohammed O.
Sherden, Nathaniel H.
Geu-Flores, Fernando
Lawson, David M.
O’Connor, Sarah E.
author_sort Kries, Hajo
collection PubMed
description The carbon skeleton of ecologically and pharmacologically important iridoid monoterpenes is formed in a reductive cyclization reaction unrelated to canonical terpene cyclization. Here we report the crystal structure of the recently discovered iridoid cyclase (Catharanthus roseus) bound to a mechanism-inspired inhibitor that illuminates substrate binding and catalytic function of the enzyme. Key features that distinguish iridoid synthase from its close homologue, progesterone 5β-reductase, are highlighted.
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spelling pubmed-46857422016-05-18 Structural determinants of reductive terpene cyclization in iridoid biosynthesis Kries, Hajo Caputi, Lorenzo Stevenson, Clare E. M. Kamileen, Mohammed O. Sherden, Nathaniel H. Geu-Flores, Fernando Lawson, David M. O’Connor, Sarah E. Nat Chem Biol Article The carbon skeleton of ecologically and pharmacologically important iridoid monoterpenes is formed in a reductive cyclization reaction unrelated to canonical terpene cyclization. Here we report the crystal structure of the recently discovered iridoid cyclase (Catharanthus roseus) bound to a mechanism-inspired inhibitor that illuminates substrate binding and catalytic function of the enzyme. Key features that distinguish iridoid synthase from its close homologue, progesterone 5β-reductase, are highlighted. 2015-11-09 2016-01 /pmc/articles/PMC4685742/ /pubmed/26551396 http://dx.doi.org/10.1038/nchembio.1955 Text en Users may view, print, copy, and download text and data-mine the content in such documents, for the purposes of academic research, subject always to the full Conditions of use:http://www.nature.com/authors/editorial_policies/license.html#terms
spellingShingle Article
Kries, Hajo
Caputi, Lorenzo
Stevenson, Clare E. M.
Kamileen, Mohammed O.
Sherden, Nathaniel H.
Geu-Flores, Fernando
Lawson, David M.
O’Connor, Sarah E.
Structural determinants of reductive terpene cyclization in iridoid biosynthesis
title Structural determinants of reductive terpene cyclization in iridoid biosynthesis
title_full Structural determinants of reductive terpene cyclization in iridoid biosynthesis
title_fullStr Structural determinants of reductive terpene cyclization in iridoid biosynthesis
title_full_unstemmed Structural determinants of reductive terpene cyclization in iridoid biosynthesis
title_short Structural determinants of reductive terpene cyclization in iridoid biosynthesis
title_sort structural determinants of reductive terpene cyclization in iridoid biosynthesis
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4685742/
https://www.ncbi.nlm.nih.gov/pubmed/26551396
http://dx.doi.org/10.1038/nchembio.1955
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