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

Kathleen A. Rising; Charisse M. Crenshaw; Hyun Jo Koo; Thangaiah Subramanian; Kareem A. H. Chehade; Courtney Starks; Keith D. Allen; Douglas A. Andres; H. Peter Spielmann; Joseph P. Noel; Joe Chappell

doi:10.1021/acschembio.5b00145

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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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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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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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.725442771.793515643 ◽

2016 ◽

Author(s):

Gregory Stephanopoulos

Keyword(s):

Farnesyl Diphosphate ◽

Aristolochene Synthase

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X-ray Crystal Structure of Aristolochene Synthase fromAspergillus terreusand Evolution of Templates for the Cyclization of Farnesyl Diphosphate†,‡

Biochemistry ◽

10.1021/bi0622524 ◽

2007 ◽

Vol 46 (7) ◽

pp. 1941-1951 ◽

Cited By ~ 110

Author(s):

Ekaterina Y. Shishova ◽

Luigi Di Costanzo ◽

David E. Cane ◽

David W. Christianson

Keyword(s):

Crystal Structure ◽

Farnesyl Diphosphate ◽

X Ray ◽

Aristolochene Synthase

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Bisabolyl-Derived Sesquiterpenes from Tobacco 5-Epi-aristolochene Synthase-Catalyzed Cyclization of (2Z,6E)-Farnesyl Diphosphate

Journal of the American Chemical Society ◽

10.1021/ja909886q ◽

2010 ◽

Vol 132 (12) ◽

pp. 4281-4289 ◽

Cited By ~ 27

Author(s):

Juan A. Faraldos ◽

Paul E. O’Maille ◽

Nikki Dellas ◽

Joseph P. Noel ◽

Robert M. Coates

Keyword(s):

Farnesyl Diphosphate ◽

Aristolochene Synthase

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X‐ray Crystal Structure of Aristolochene Synthase from Aspergillus terreus and Evolution of Templates for the Cyclization of Farnesyl Diphosphate

The FASEB Journal ◽

10.1096/fasebj.21.6.lb14-a ◽

2007 ◽

Vol 21 (6) ◽

Author(s):

Ekaterina Y Shishova ◽

Luigi Di Costanzo ◽

David E Cane ◽

David W Christianson

Keyword(s):

Crystal Structure ◽

Aspergillus Terreus ◽

Farnesyl Diphosphate ◽

X Ray ◽

Aristolochene Synthase

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Faculty Opinions recommendation of The metabolic imbalance underlying lesion formation in Arabidopsis thaliana overexpressing farnesyl diphosphate synthase (isoform 1S) leads to oxidative stress and is triggered by the developmental decline of endogenous HMGR activity.

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

10.3410/f.1023123.264815 ◽

2005 ◽

Author(s):

Ramón Serrano

Keyword(s):

Oxidative Stress ◽

Arabidopsis Thaliana ◽

Farnesyl Diphosphate ◽

Farnesyl Diphosphate Synthase ◽

Lesion Formation ◽

Metabolic Imbalance ◽

Hmgr Activity

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Identification of a 6-base pair element involved in the sterol-mediated transcriptional regulation of farnesyl diphosphate synthase.

Journal of Biological Chemistry ◽

10.1016/s0021-9258(17)31519-3 ◽

1994 ◽

Vol 269 (40) ◽

pp. 25212-25218 ◽

Cited By ~ 4

Author(s):

D.H. Spear ◽

J. Ericsson ◽

S.M. Jackson ◽

P.A. Edwards

Keyword(s):

Transcriptional Regulation ◽

Base Pair ◽

Farnesyl Diphosphate ◽

Farnesyl Diphosphate Synthase

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Maize cDNAs Expressed in Endosperm Encode Functional Farnesyl Diphosphate Synthase with Geranylgeranyl Diphosphate Synthase Activity

PLANT PHYSIOLOGY ◽

10.1104/pp.106.077008 ◽

2006 ◽

Vol 141 (1) ◽

pp. 220-231 ◽

Cited By ~ 31

Author(s):

Miguel Cervantes-Cervantes ◽

Cynthia E. Gallagher ◽

Changfu Zhu ◽

Eleanore T. Wurtzel

Keyword(s):

Farnesyl Diphosphate ◽

Farnesyl Diphosphate Synthase ◽

Geranylgeranyl Diphosphate Synthase ◽

Geranylgeranyl Diphosphate

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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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