Mechanistic Insights from the Binding of Substrate and Carbocation Intermediate Analogues to Aristolochene Synthase

Mengbin Chen; Naeemah Al-lami; Marine Janvier; Edward L. D’Antonio; Juan A. Faraldos; David E. Cane; Rudolf K. Allemann; David W. Christianson

doi:10.1021/bi400691v

Mechanistic Insights from the Binding of Substrate and Carbocation Intermediate Analogues to Aristolochene Synthase

Biochemistry ◽

10.1021/bi400691v ◽

2013 ◽

Vol 52 (32) ◽

pp. 5441-5453 ◽

Cited By ~ 39

Author(s):

Mengbin Chen ◽

Naeemah Al-lami ◽

Marine Janvier ◽

Edward L. D’Antonio ◽

Juan A. Faraldos ◽

...

Keyword(s):

Aristolochene Synthase

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Faculty Opinions recommendation of Formation of a Novel Macrocyclic Alkaloid from the Unnatural Farnesyl Diphosphate Analogue Anilinogeranyl Diphosphate by 5-Epi-Aristolochene Synthase.

Faculty Opinions – Post-Publication Peer Review of the Biomedical Literature ◽

10.3410/f.725442771.793512383 ◽

2015 ◽

Author(s):

Jon Thorson

Keyword(s):

Farnesyl Diphosphate ◽

Aristolochene Synthase

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Evidence for Differential Folding of Farnesyl Pyrophosphate in the Active Site of Aristolochene Synthase: A Single-Point Mutation Converts Aristolochene Synthase into an (E)-β-Farnesene Synthase†

Biochemistry ◽

10.1021/bi034410m ◽

2003 ◽

Vol 42 (25) ◽

pp. 7741-7747 ◽

Cited By ~ 44

Author(s):

Athina Deligeorgopoulou ◽

Rudolf K. Allemann

Keyword(s):

Point Mutation ◽

Active Site ◽

Single Point ◽

Single Point Mutation ◽

Farnesyl Pyrophosphate ◽

Aristolochene Synthase

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6- and 14-Fluoro farnesyl diphosphate: mechanistic probes for the reaction catalysed by aristolochene synthase

Organic & Biomolecular Chemistry ◽

10.1039/b817194g ◽

2009 ◽

Vol 7 (5) ◽

pp. 962 ◽

Cited By ~ 27

Author(s):

David J. Miller ◽

Fanglei Yu ◽

David W. Knight ◽

Rudolf K. Allemann

Keyword(s):

Farnesyl Diphosphate ◽

Aristolochene Synthase

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The role of aristolochene synthase in diphosphate activation

Chemical Communications ◽

10.1039/c2cc17588f ◽

2012 ◽

Vol 48 (26) ◽

pp. 3230 ◽

Cited By ~ 13

Author(s):

Juan A. Faraldos ◽

Veronica Gonzalez ◽

Rudolf K. Allemann

Keyword(s):

Aristolochene Synthase

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Stabilisation of eudesmane cation by tryptophan 334 during aristolochene synthase catalysisElectronic Supplementary Information (ESI) available: GC profiles of co-injections of germacrene A from ASW334F and ASW334V with authentic germacrene A; mass spectra of germacrene A produced by ASW334V and of an authentic sample; mass spectra of valencene produced by ASW334F and of an authentic sample. See http://www.rsc.org/suppdata/cc/b3/b306867f/

Chemical Communications ◽

10.1039/b306867f ◽

2003 ◽

pp. 2162 ◽

Cited By ~ 27

Author(s):

Athina Deligeorgopoulou ◽

Susan E. Taylor ◽

Silvia Forcat ◽

Rudolf K. Allemann

Keyword(s):

Mass Spectra ◽

Authentic Sample ◽

Supplementary Information ◽

Sample Mass ◽

Aristolochene Synthase

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Formation of a Novel Macrocyclic Alkaloid from the Unnatural Farnesyl Diphosphate Analogue Anilinogeranyl Diphosphate by 5-Epi-Aristolochene Synthase

ACS Chemical Biology ◽

10.1021/acschembio.5b00145 ◽

2015 ◽

Vol 10 (7) ◽

pp. 1729-1736 ◽

Cited By ~ 21

Author(s):

Kathleen A. Rising ◽

Charisse M. Crenshaw ◽

Hyun Jo Koo ◽

Thangaiah Subramanian ◽

Kareem A. H. Chehade ◽

...

Keyword(s):

Farnesyl Diphosphate ◽

Aristolochene Synthase

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Inhibition of (+)-Aristolochene Synthase with Iminium Salts Resembling Eudesmane Cation

Organic Letters ◽

10.1021/ol2000843 ◽

2011 ◽

Vol 13 (5) ◽

pp. 1202-1205 ◽

Cited By ~ 18

Author(s):

Juan A. Faraldos ◽

Rudolf K. Allemann

Keyword(s):

Iminium Salts ◽

Aristolochene Synthase

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Tyrosine 92 of aristolochene synthase directs cyclisation of farnesyl pyrophosphateElectronic supplementary information (ESI) available: GC-profiles of co-injections of 4 from ASY92V and authentic material and mass spectra of 4 produced by ASY92V and an authentic sample. See http://www.rsc.org/suppdata/cc/b2/b206517g/

Chemical Communications ◽

10.1039/b206517g ◽

2002 ◽

pp. 2384-2385 ◽

Cited By ~ 23

Author(s):

Melanie J. Calvert ◽

Susan E. Taylor ◽

Rudolf K. Allemann

Keyword(s):

Mass Spectra ◽

Authentic Sample ◽

Supplementary Information ◽

Authentic Material ◽

Aristolochene Synthase

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Demonstration of Germacrene A as an Intermediate in 5-Epi-aristolochene Synthase Catalysis

Journal of the American Chemical Society ◽

10.1021/ja993584h ◽

2000 ◽

Vol 122 (9) ◽

pp. 1861-1866 ◽

Cited By ~ 78

Author(s):

Kathleen A. Rising ◽

Courtney M. Starks ◽

Joseph P. Noel ◽

Joseph Chappell

Keyword(s):

Aristolochene Synthase

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Fusion of farnesyldiphosphate synthase and epi -aristolochene synthase, a sesquiterpene cyclase involved in capsidiol biosynthesis in Nicotiana tabacum

European Journal of Biochemistry ◽

10.1046/j.1432-1033.2002.03044.x ◽

2002 ◽

Vol 269 (14) ◽

pp. 3570-3577 ◽

Cited By ~ 43

Author(s):

Maria Brodelius ◽

Anneli Lundgren ◽

Per Mercke ◽

Peter E. Brodelius

Keyword(s):

Nicotiana Tabacum ◽

Aristolochene Synthase ◽

Sesquiterpene Cyclase

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