Journal of the American Chemical Society · 2011 · 78 citations · 35 references
Asymmetric CatalysisBiosynthesisBioorganic ChemistryEngineeringBiochemistryNatural SciencesBiocatalysisEnzyme CatalysisMolecular BiologyEnzyme Dimethylallyltryptophan SynthaseNatural Product BiosynthesisErgot Alkaloid BiosynthesisCatalysisReaction IntermediateChemical BiologyStructure-function Enzyme KineticsCope RearrangementProtein Biosynthesis
The enzyme dimethylallyltryptophan synthase catalyzes the "normal" prenylation of Trp at C-4 in the first step of ergot alkaloid biosynthesis. The Lys174Ala mutant is found to produce a hexahydropyrroloindole alkaloid that is "reverse-prenylated" at C-3 as its major product. This is interpreted as evidence in support of a mechanism that involves an initial "reverse-prenylation" at C-3, followed by a Cope rearrangement and rearomatization.
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Enzyme-catalysed [4+2] cycloaddition is a key step in the biosynthesis of spinosyn A
Hak Joong Kim, Mark W. Ruszczycky, Sei-hyun Choi et al. · Nature · 2011 · 312 citations
Kristopher M. Depew, Stephen P. Marsden, Danuta Zatorska et al. · Journal of the American Chemical Society · 1999 · 244 citations
Bioorganic Chemistry, Mdr Reversal Agents, Organic Chemistry +17