Literature DB >> 22738258

Effect of isotopically sensitive branching on product distribution for pentalenene synthase: support for a mechanism predicted by quantum chemistry.

Liansuo Zu1, Meimei Xu, Michael W Lodewyk, David E Cane, Reuben J Peters, Dean J Tantillo.   

Abstract

Mechanistic proposals for the carbocation cascade reaction leading to the tricyclic sesquiterpene pentalenene are assessed in light of the results of isotopically sensitive branching experiments with the H309A mutant of pentalenene synthase. These experimental results support a mechanism for pentalenene formation involving a 7-protoilludyl cation whose intermediacy was first predicted using quantum-chemical calculations.

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Year:  2012        PMID： 22738258      PMCID： PMC3402234          DOI： 10.1021/ja3043245

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  22 in total

1.  Pentalenene synthase. Analysis of active site residues by site-directed mutagenesis.

Authors:  Myriam Seemann; Guangzhi Zhai; Jan-Willem de Kraker; Chiana M Paschall; David W Christianson; David E Cane
Journal:  J Am Chem Soc       Date:  2002-07-03       Impact factor: 15.419

2.  Quantum chemical dissection of the classic terpinyl/pinyl/bornyl/camphyl cation conundrum-the role of pyrophosphate in manipulating pathways to monoterpenes.

Authors:  Young J Hong; Dean J Tantillo
Journal:  Org Biomol Chem       Date:  2010-08-19       Impact factor: 3.876

3.  Sesquiterpenes from lippia integrifolia essential Oil

Authors: 
Journal:  J Nat Prod       Date:  1999-05       Impact factor: 4.050

4.  Theoretical studies on farnesyl cation cyclization: pathways to pentalenene.

Authors:  Pradeep Gutta; Dean J Tantillo
Journal:  J Am Chem Soc       Date:  2006-05-10       Impact factor: 15.419

5.  X-ray crystal structure of aristolochene synthase from Aspergillus terreus and evolution of templates for the cyclization of farnesyl diphosphate.

Authors:  Ekaterina Y Shishova; Luigi Di Costanzo; David E Cane; David W Christianson
Journal:  Biochemistry       Date:  2007-01-30       Impact factor: 3.162

6.  Site-Directed Mutagenesis of the Sterol Methyl Transferase Active Site from Saccharomyces cerevisiae Results in Formation of Novel 24-Ethyl Sterols.

Authors:  W. David Nes; Brian S. McCourt; Julie A. Marshall; Jianzhong Ma; Allen L. Dennis; Monica Lopez; Haoxia Li; Ling He
Journal:  J Org Chem       Date:  1999-03-05       Impact factor: 4.354

7.  Electrostatic effects on (di)terpene synthase product outcome.

Authors:  Ke Zhou; Reuben J Peters
Journal:  Chem Commun (Camb)       Date:  2011-02-08       Impact factor: 6.222

8.  Monoterpene biosynthesis: isotope effects associated with bicyclic olefin formation catalyzed by pinene synthases from sage (Salvia officinalis).

Authors:  K C Wagschal; H J Pyun; R M Coates; R Croteau
Journal:  Arch Biochem Biophys       Date:  1994-02-01       Impact factor: 4.013

9.  Alternative termination chemistries utilized by monoterpene cyclases: chimeric analysis of bornyl diphosphate, 1,8-cineole, and sabinene synthases.

Authors:  Reuben J Peters; Rodney B Croteau
Journal:  Arch Biochem Biophys       Date:  2003-09-15       Impact factor: 4.013

10.  Mechanism and stereochemistry of the germacradienol/germacrene D synthase of Streptomyces coelicolor A3(2).

Authors:  Xiaofei He; David E Cane
Journal:  J Am Chem Soc       Date:  2004-03-10       Impact factor: 15.419
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  25 in total

1.  Purification, crystallization and preliminary X-ray diffraction analysis of Omp6, a protoilludene synthase from Omphalotus olearius.

Authors:  Maureen B Quin; Grayson Wawrzyn; Claudia Schmidt-Dannert
Journal:  Acta Crystallogr Sect F Struct Biol Cryst Commun       Date:  2013-04-30

2.  Computational-guided discovery and characterization of a sesquiterpene synthase from Streptomyces clavuligerus.

Authors:  Jeng-Yeong Chow; Bo-Xue Tian; Gurusankar Ramamoorthy; Brandan S Hillerich; Ronald D Seidel; Steven C Almo; Matthew P Jacobson; C Dale Poulter
Journal:  Proc Natl Acad Sci U S A       Date:  2015-04-21       Impact factor: 11.205

3.  Nature as organic chemist.

Authors:  David E Cane
Journal:  J Antibiot (Tokyo)       Date:  2016-07       Impact factor: 2.649

Review 4.  Structural and Chemical Biology of Terpenoid Cyclases.

Authors:  David W Christianson
Journal:  Chem Rev       Date:  2017-08-25       Impact factor: 60.622

5.  Predicting Productive Binding Modes for Substrates and Carbocation Intermediates in Terpene Synthases-Bornyl Diphosphate Synthase as a Representative Case.

Authors:  Terrence E O'Brien; Steven J Bertolani; Yue Zhang; Justin B Siegel; Dean J Tantillo
Journal:  ACS Catal       Date:  2018-03-08       Impact factor: 13.084

6.  Biochemical characterization of the castor bean ent-kaurene synthase(-like) family supports quantum chemical view of diterpene cyclization.

Authors:  Alana J Jackson; David M Hershey; Taylor Chesnut; Meimei Xu; Reuben J Peters
Journal:  Phytochemistry       Date:  2014-05-05       Impact factor: 4.072

Review 7.  Terpenoid synthase structures: a so far incomplete view of complex catalysis.

Authors:  Yang Gao; Richard B Honzatko; Reuben J Peters
Journal:  Nat Prod Rep       Date:  2012-08-21       Impact factor: 13.423

Review 8.  Traversing the fungal terpenome.

Authors:  Maureen B Quin; Christopher M Flynn; Claudia Schmidt-Dannert
Journal:  Nat Prod Rep       Date:  2014-10       Impact factor: 13.423

9.  Moonlighting Metals: Insights into Regulation of Cyclization Pathways in Fungal Δ(6) -Protoilludene Sesquiterpene Synthases.

Authors:  Maureen B Quin; Stephen N Michel; Claudia Schmidt-Dannert
Journal:  Chembiochem       Date:  2015-09-01       Impact factor: 3.164

10.  Crystal Structure of Cucumene Synthase, a Terpenoid Cyclase That Generates a Linear Triquinane Sesquiterpene.

Authors:  Patrick N Blank; Travis A Pemberton; Jeng-Yeong Chow; C Dale Poulter; David W Christianson
Journal:  Biochemistry       Date:  2018-10-22       Impact factor: 3.162
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