Biosynthetic insights provided by unusual sesterterpenes from the medicinal herb Aletris farinosa

Victoria L. Challinor, Ryne C. Johnston, Paul V. Bernhardt, Reginald P. Lehmann, Elizabeth H. Krenske and James J. De Voss

Chem. Sci., 2015, 6, 5740
DOI: 10.1039/C5SC02056E

Catalytic promiscuity of the non-native FPP substrate in the TEAS enzyme: non-negligible flexibility of the carbocation intermediate

Fan Zhang, Yong-Heng Wang, Xiaowen Tang and Ruibo Wu

Phys. Chem. Chem. Phys., 2018, 20, 15061
DOI: 10.1039/C8CP02262C

Bacterial terpene cyclases

Jeroen S. Dickschat

Nat. Prod. Rep., 2016, 33, 87
DOI: 10.1039/C5NP00102A

Mechanistically informed predictions of binding modes for carbocation intermediates of a sesquiterpene synthase reaction

T. E. O'Brien, S. J. Bertolani, D. J. Tantillo and J. B. Siegel

Chem. Sci., 2016, 7, 4009
DOI: 10.1039/C6SC00635C

Preorganization and Cooperation for Highly Efficient and Reversible Capture of Low‐Concentration CO2 by Ionic Liquids

Yanjie Huang, Guokai Cui, Yuling Zhao, Huiyong Wang, Zhiyong Li, Sheng Dai and Jianji Wang

Angewandte Chemie, 2017, 129, 13478
DOI: 10.1002/ange.201706280

Crystal Structure and Mechanistic Molecular Modeling Studies of Mycobacterium tuberculosis Diterpene Cyclase Rv3377c

Yue Zhang, Lisa M. Prach, Terrence E. O’Brien, Frank DiMaio, Daniil M. Prigozhin, Jacob E. Corn, Tom Alber, Justin B. Siegel and Dean J. Tantillo

Biochemistry, 2020, 59, 4507
DOI: 10.1021/acs.biochem.0c00762

Switchable Synthetic Strategy toward Trisubstituted and Tetrasubstituted Exocyclic Alkenes

Sen Zhou, Fangyuan Yuan, Minjie Guo, Guangwei Wang, Xiangyang Tang and Wentao Zhao

Org. Lett., 2018, 20, 6710
DOI: 10.1021/acs.orglett.8b02801

Insights Into the Bifunctional Aphidicolan-16-ß-ol Synthase Through Rapid Biomolecular Modeling Approaches

Max Hirte, Nicolas Meese, Michael Mertz, Monika Fuchs and Thomas B. Brück

Front. Chem., 2018, 6
DOI: 10.3389/fchem.2018.00101

Concertedness and Activation Energy Control by Distal Methyl Group during Ring Contraction/Expansion in Scalarane‐Type Sesterterpenoid Biosynthesis

Hajime Sato and Moe Nakano

Chemistry A European J, 2023, 29
DOI: 10.1002/chem.202203076

Montecrinanes A–C: Triterpenes with an Unprecedented Rearranged Tetracyclic Skeleton from Celastrus vulcanicola. Insights into Triterpenoid Biosynthesis Based on DFT Calculations

Martín Purino, Alejandro E. Ardiles, Oliver Callies, Ignacio A. Jiménez and Isabel L. Bazzocchi

Chemistry A European J, 2016, 22, 7582
DOI: 10.1002/chem.201600294

First principles model calculations of the biosynthetic pathway in selinadiene synthase

Susanta Das, Mudit Dixit and Dan Thomas Major

Bioorganic & Medicinal Chemistry, 2016, 24, 4867
DOI: 10.1016/j.bmc.2016.07.002

Dynamic behavior of rearranging carbocations – implications for terpene biosynthesis

Stephanie R Hare and Dean J Tantillo

Beilstein J. Org. Chem., 2016, 12, 377
DOI: 10.3762/bjoc.12.41

Decoding Catalysis by Terpene Synthases

Joshua N. Whitehead, Nicole G. H. Leferink, Linus O. Johannissen, Sam Hay and Nigel S. Scrutton

ACS Catal., 2023, 13, 12774
DOI: 10.1021/acscatal.3c03047

Stereochemical investigations on the biosynthesis of achiral (Z)-γ-bisabolene in Cryptosporangium arvum

Jan Rinkel and Jeroen S Dickschat

Beilstein J. Org. Chem., 2019, 15, 789
DOI: 10.3762/bjoc.15.75

Revision of the Peniroquesine Biosynthetic Pathway by Retro-Biosynthetic Theoretical Analysis: Ring Strain Controls the Unique Carbocation Rearrangement Cascade

Taro Matsuyama, Ko Togashi, Moe Nakano, Hajime Sato and Masanobu Uchiyama

JACS Au, 2023, 3, 1596
DOI: 10.1021/jacsau.3c00039

Reply to Comment on “Substrate Folding Modes in Trichodiene Synthase: A Determinant of Chemo- and Stereoselectivity”

Yong-Heng Wang, Fan Zhang, Jingwei Zhou, Hujun Xie and Ruibo Wu

ACS Catal., 2018, 8, 1363
DOI: 10.1021/acscatal.7b03906

Delocalization of Charge and Electron Density in the Humulyl Cation—Implications for Terpene Biosynthesis

Trevor A. Hamlin, Christian S. Hamann and Dean J. Tantillo

J. Org. Chem., 2015, 80, 4046
DOI: 10.1021/acs.joc.5b00381

Enzyme Promiscuity versus Fidelity in Two Sesquiterpene Cyclases (TEAS versus ATAS)

Fan Zhang, Tianyue An, Xiaowen Tang, Jiachen Zi, Hai-Bin Luo and Ruibo Wu

ACS Catal., 2020, 10, 1470
DOI: 10.1021/acscatal.9b05051

Synthesis of Exocyclic Trisubstituted Alkenes via Nickel‐ Catalyzed Kumada‐Type Cross‐Coupling Reaction of gem‐ Difluoroalkenes with Di‐Grignard Reagents

Wenpeng Dai, Xuxue Zhang, Juan Zhang, Yingyin Lin and Song Cao

Adv Synth Catal, 2016, 358, 183
DOI: 10.1002/adsc.201500889

Biosynthesis and Conformational Properties of the Irregular Sesquiterpenoids Isothapsadiene and β-Isothapsenol

Laurence G. Cool, Karl E. Vermillion, Gary R. Takeoka, Selina C. Wang and Dean J. Tantillo

J. Org. Chem., 2018, 83, 5724
DOI: 10.1021/acs.joc.8b00800

Carbocations and the Complex Flavor and Bouquet of Wine: Mechanistic Aspects of Terpene Biosynthesis in Wine Grapes

Henry Wedler, Ryan Pemberton and Dean Tantillo

Molecules, 2015, 20, 10781
DOI: 10.3390/molecules200610781

Tension between Internal and External Modes of Stabilization in Carbocations Relevant to Terpene Biosynthesis: Modulating Minima Depth via C–H···π Interactions

Young J. Hong and Dean J. Tantillo

Org. Lett., 2015, 17, 5388
DOI: 10.1021/acs.orglett.5b02740

Protonation-Dependent Diphosphate Cleavage in FPP Cyclases and Synthases

Fan Zhang, Nanhao Chen, Jingwei Zhou and Ruibo Wu

ACS Catal., 2016, 6, 6918
DOI: 10.1021/acscatal.6b02096

Navigating Past a Fork in the Road: Carbocation−π Interactions Can Manipulate Dynamic Behavior of Reactions Facing Post-Transition-State Bifurcations

Stephanie R. Hare, Ryan P. Pemberton and Dean J. Tantillo

J. Am. Chem. Soc., 2017, 139, 7485
DOI: 10.1021/jacs.7b01042

Decarboxylation Facilitated by Carbocation Formation and Rearrangement during Steam Distillation of Vetiver Oil

Henry B. Wedler, T. Newman and Dean J. Tantillo

J. Nat. Prod., 2016, 79, 2744
DOI: 10.1021/acs.jnatprod.6b00348

Molecular Dynamics Simulations Elucidate Conformational Dynamics Responsible for the Cyclization Reaction in TEAS

Fan Zhang, Nanhao Chen and Ruibo Wu

J. Chem. Inf. Model., 2016, 56, 877
DOI: 10.1021/acs.jcim.6b00091

Position‐Specific Mass Shift Analysis: A Systematic Method for Investigating the EI‐MS Fragmentation Mechanism of epi‐Isozizaene

Patrick Rabe, Tim A. Klapschinski and Jeroen S. Dickschat

ChemBioChem, 2016, 17, 1333
DOI: 10.1002/cbic.201600237

Biomimetic Synthesis of Nor‐Cedrene and Nor‐Isozizaene Sesquiterpenoids and Exploration of Their Olfactive Properties

Tony Georgiev and Nicolas Armanino

Chemistry A European J, 2022, 28
DOI: 10.1002/chem.202201037