Robert M. Coates
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View article: Synthesis of Methylerythritol Phosphate Analogues and Their Evaluation as Alternate Substrates for IspDF and IspE from <i>Agrobacterium tumefaciens</i>
Synthesis of Methylerythritol Phosphate Analogues and Their Evaluation as Alternate Substrates for IspDF and IspE from <i>Agrobacterium tumefaciens</i> Open
The methylerythritol phosphate biosynthetic pathway, found in most Bacteria, some parasitic protists, and plant chloroplasts, converts D-glyceraldehyde phosphate and pyruvate to isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (…
View article: Alternative Synthesis of the Colorado Potato Beetle Pheromone
Alternative Synthesis of the Colorado Potato Beetle Pheromone Open
A concise preparation of the pheromone secreted by the male Colorado potato beetle [viz. (3S)-1,3-dihydroxy-3,7-dimethyl-6-octen-2-one] was accomplished in four steps starting from 2-fluoronerol or 2-fluorogeraniol. The key step in the syn…
View article: Formation of the Unusual Semivolatile Diterpene Rhizathalene by the <i>Arabidopsis</i> Class I Terpene Synthase TPS08 in the Root Stele Is Involved in Defense against Belowground Herbivory
Formation of the Unusual Semivolatile Diterpene Rhizathalene by the <i>Arabidopsis</i> Class I Terpene Synthase TPS08 in the Root Stele Is Involved in Defense against Belowground Herbivory Open
Secondary metabolites are major constituents of plant defense against herbivore attack. Relatively little is known about the cell type–specific formation and antiherbivore activities of secondary compounds in roots despite the substantial …
View article: 2-Azapinanes: Aza Analogues of the Enantiomeric Pinyl Carbocation Intermediates in Pinene Biosynthesis
2-Azapinanes: Aza Analogues of the Enantiomeric Pinyl Carbocation Intermediates in Pinene Biosynthesis Open
The enantiomeric 2-azapinanes, aza analogues of the pinyl carbocation intermediates in pinene biosynthesis, were synthesized from (-)- and (+)-cis-pinonic acids. The individual reactions in the 5-step sequence were Beckmann rearrangement o…
View article: CCDC 835899: Experimental Crystal Structure Determination
CCDC 835899: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: A Single Residue Switch for Mg2+-dependent Inhibition Characterizes Plant Class II Diterpene Cyclases from Primary and Secondary Metabolism
A Single Residue Switch for Mg2+-dependent Inhibition Characterizes Plant Class II Diterpene Cyclases from Primary and Secondary Metabolism Open
Class II diterpene cyclases mediate the acid-initiated cycloisomerization reaction that serves as the committed step in biosynthesis of the large class of labdane-related diterpenoid natural products, which includes the important gibberell…
View article: Structural Elucidation of Cisoid and Transoid Cyclization Pathways of a Sesquiterpene Synthase Using 2-Fluorofarnesyl Diphosphates
Structural Elucidation of Cisoid and Transoid Cyclization Pathways of a Sesquiterpene Synthase Using 2-Fluorofarnesyl Diphosphates Open
Sesquiterpene skeletal complexity in nature originates from the enzyme-catalyzed ionization of (trans,trans)-farnesyl diphosphate (FPP) (1a) and subsequent cyclization along either 2,3-transoid or 2,3-cisoid farnesyl cation pathways. Tobac…
View article: Scope and Mechanism of Intramolecular Aziridination of Cyclopent-3-enyl-methylamines to 1-Azatricyclo[2.2.1.0<sup>2,6</sup>]heptanes with Lead Tetraacetate
Scope and Mechanism of Intramolecular Aziridination of Cyclopent-3-enyl-methylamines to 1-Azatricyclo[2.2.1.0<sup>2,6</sup>]heptanes with Lead Tetraacetate Open
A series of seven cyclopent-3-en-1-ylmethylamines bearing one, two, or three methyl substituents at the C2, C3, C4, or C(alpha) positions, including the unsubstituted parent, was accessed by ring-closing metatheses of alpha,alpha-diallylac…
View article: Characteristic Flavonoids from <i>Acacia burkittii</i> and <i>A. Acuminata</i> Heartwoods and their Differential Cytotoxicit to Normal and Leukemia Cells
Characteristic Flavonoids from <i>Acacia burkittii</i> and <i>A. Acuminata</i> Heartwoods and their Differential Cytotoxicit to Normal and Leukemia Cells Open
Bioassay-guided fractionation of extracts from Acacia burkittii and A. acuminata heartwoods against an L1210 (mouse lymphoma) cell line led to the isolation of two flavan-3,4-diols, melacacidin (1) and isomelacacidin (2), and three flavono…
View article: X-ray Crystallographic Studies of Substrate Binding to Aristolochene Synthase Suggest a Metal Ion Binding Sequence for Catalysis
X-ray Crystallographic Studies of Substrate Binding to Aristolochene Synthase Suggest a Metal Ion Binding Sequence for Catalysis Open
The universal sesquiterpene precursor, farnesyl diphosphate (FPP), is cyclized in an Mg(2+)-dependent reaction catalyzed by the tetrameric aristolochene synthase from Aspergillus terreus to form the bicyclic hydrocarbon aristolochene and a…
View article: CCDC 673319: Experimental Crystal Structure Determination
CCDC 673319: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 673320: Experimental Crystal Structure Determination
CCDC 673320: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 673318: Experimental Crystal Structure Determination
CCDC 673318: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: 16-Aza-<i>ent</i>-beyerane and 16-Aza-<i>ent</i>-trachylobane: Potent Mechanism-Based Inhibitors of Recombinant <i>ent</i>-Kaurene Synthase from <i>Arabidopsis thaliana</i>
16-Aza-<i>ent</i>-beyerane and 16-Aza-<i>ent</i>-trachylobane: Potent Mechanism-Based Inhibitors of Recombinant <i>ent</i>-Kaurene Synthase from <i>Arabidopsis thaliana</i> Open
The secondary ent-beyeran-16-yl carbocation (7) is a key branch point intermediate in mechanistic schemes to rationalize the cyclic structures of many tetra- and pentacyclic diterpenes, including ent-beyerene, ent-kaurene, ent-trachylobane…
View article: Functional Characterization of Premnaspirodiene Oxygenase, a Cytochrome P450 Catalyzing Regio- and Stereo-specific Hydroxylations of Diverse Sesquiterpene Substrates
Functional Characterization of Premnaspirodiene Oxygenase, a Cytochrome P450 Catalyzing Regio- and Stereo-specific Hydroxylations of Diverse Sesquiterpene Substrates Open
Solavetivone, a potent antifungal phytoalexin, is derived from a vetispirane-type sesquiterpene, premnaspirodiene, by a putative regio- and stereo-specific hydroxylation, followed by a second oxidation to yield the alpha,beta-unsaturated k…
View article: Probing the Role of the DXDD Motif in Class II Diterpene Cyclases
Probing the Role of the DXDD Motif in Class II Diterpene Cyclases Open
On common ground. An epoxy analogue of geranylgeranyl diphosphate was used together with site-directed mutagenesis to provide evidence that the DXDD motif in class II diterpene cyclases is involved in CC double-bond protonation (see schem…
View article: Structure of limonene synthase, a simple model for terpenoid cyclase catalysis
Structure of limonene synthase, a simple model for terpenoid cyclase catalysis Open
The crystal structure of (4 S )-limonene synthase from Mentha spic ata , a metal ion-dependent monoterpene cyclase that catalyzes the coupled isomerization and cyclization of geranyl diphosphate, is reported at 2.7-Å; resolution in two for…
View article: CCDC 269094: Experimental Crystal Structure Determination
CCDC 269094: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 278060: Experimental Crystal Structure Determination
CCDC 278060: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 278592: Experimental Crystal Structure Determination
CCDC 278592: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 278061: Experimental Crystal Structure Determination
CCDC 278061: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 278059: Experimental Crystal Structure Determination
CCDC 278059: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 278150: Experimental Crystal Structure Determination
CCDC 278150: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …