Literature DB >> 35385666

Deceptive Complexity in Formation of Cleistantha-8,12-diene.

Jin Liang1,2, Amy T Merrill3, Croix J Laconsay3, Anwei Hou4, Qingyu Pu1, Jeroen S Dickschat4, Dean J Tantillo3, Qiang Wang1, Reuben J Peters2.   

Abstract

A barley diterpene synthase (HvKSL4) was found to produce (14S)-cleistantha-8,12-diene (1). Formation of the nearly planar cyclohexa-1,4-diene configuration leaves the ring poised for aromatization, but necessitates a deceptively complicated series of rearrangements steered through a complex energetic landscape, as elucidated here through quantum chemical calculations and labeling studies.

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Year:  2022        PMID： 35385666      PMCID： PMC9040526          DOI： 10.1021/acs.orglett.2c00680

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.072


  19 in total

Review 1.  Two rings in them all: the labdane-related diterpenoids.

Authors:  Reuben J Peters
Journal:  Nat Prod Rep       Date:  2010-10-01       Impact factor: 13.423

2.  Mechanistic Investigations of Two Bacterial Diterpene Cyclases: Spiroviolene Synthase and Tsukubadiene Synthase.

Authors:  Patrick Rabe; Jan Rinkel; Etilia Dolja; Thomas Schmitz; Britta Nubbemeyer; T Hoang Luu; Jeroen S Dickschat
Journal:  Angew Chem Int Ed Engl       Date:  2017-01-31       Impact factor: 15.336

3.  Biosynthetic consequences of multiple sequential post-transition-state bifurcations.

Authors:  Young Joo Hong; Dean J Tantillo
Journal:  Nat Chem       Date:  2014-01-19       Impact factor: 24.427

4.  A Branched Diterpene Cascade: The Mechanism of Spinodiene Synthase from Saccharopolyspora spinosa.

Authors:  Jan Rinkel; Lukas Lauterbach; Jeroen S Dickschat
Journal:  Angew Chem Int Ed Engl       Date:  2018-12-06       Impact factor: 15.336

Review 5.  Specialized diterpenoid metabolism in monocot crops: Biosynthesis and chemical diversity.

Authors:  Katherine M Murphy; Philipp Zerbe
Journal:  Phytochemistry       Date:  2020-02-06       Impact factor: 4.072

6.  Functional characterization of wheat copalyl diphosphate synthases sheds light on the early evolution of labdane-related diterpenoid metabolism in the cereals.

Authors:  Yisheng Wu; Ke Zhou; Tomonobu Toyomasu; Chizu Sugawara; Madoka Oku; Shiho Abe; Masami Usui; Wataru Mitsuhashi; Makiko Chono; Peter M Chandler; Reuben J Peters
Journal:  Phytochemistry       Date:  2012-09-23       Impact factor: 4.072

7.  Functional characterization of wheat ent-kaurene(-like) synthases indicates continuing evolution of labdane-related diterpenoid metabolism in the cereals.

Authors:  Ke Zhou; Meimei Xu; Mollie Tiernan; Qian Xie; Tomonobu Toyomasu; Chizu Sugawara; Madoka Oku; Masami Usui; Wataru Mitsuhashi; Makiko Chono; Peter M Chandler; Reuben J Peters
Journal:  Phytochemistry       Date:  2012-09-22       Impact factor: 4.072

8.  Piriformospora indica requires kaurene synthase activity for successful plant colonization.

Authors:  Liang Li; Xi Chen; Chaoyang Ma; Hongqing Wu; Shuting Qi
Journal:  Plant Physiol Biochem       Date:  2016-02-16       Impact factor: 4.270

Review 9.  To gibberellins and beyond! Surveying the evolution of (di)terpenoid metabolism.

Authors:  Jiachen Zi; Sibongile Mafu; Reuben J Peters
Journal:  Annu Rev Plant Biol       Date:  2014-01-22       Impact factor: 26.379

10.  A (conditional) role for labdane-related diterpenoid natural products in rice stomatal closure.

Authors:  Juan Zhang; Riqing Li; Meimei Xu; Rachel I Hoffmann; Yushi Zhang; Bo Liu; Mingcai Zhang; Bing Yang; Zhaohu Li; Reuben J Peters
Journal:  New Phytol       Date:  2021-02-12       Impact factor: 10.151
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