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Identification of a Pentaketide Stilbene Produced by a Type III Polyketide Synthase from Pinus sylvestris and Characterisation of Free Coenzyme A Intermediates

Identification of a Pentaketide Stilbene Produced by a Type III Polyketide Synthase from Pinus sylvestris and Characterisation of Free Coenzyme A Intermediates

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LI, Tsung-Lin, Dieter SPITELLER, Jonathan B. SPENCER, 2009. Identification of a Pentaketide Stilbene Produced by a Type III Polyketide Synthase from Pinus sylvestris and Characterisation of Free Coenzyme A Intermediates. In: ChemBioChem. 10(5), pp. 896-901. ISSN 1439-4227. eISSN 1439-7633

@article{Li2009-03-23Ident-15424, title={Identification of a Pentaketide Stilbene Produced by a Type III Polyketide Synthase from Pinus sylvestris and Characterisation of Free Coenzyme A Intermediates}, year={2009}, doi={10.1002/cbic.200800840}, number={5}, volume={10}, issn={1439-4227}, journal={ChemBioChem}, pages={896--901}, author={Li, Tsung-Lin and Spiteller, Dieter and Spencer, Jonathan B.} }

Spiteller, Dieter Li, Tsung-Lin eng deposit-license Spencer, Jonathan B. 2011-10-19T08:19:42Z Publ. in: ChemBioChem ; 10 (2009), 5. - pp. 896-901 By miscounting the number of malonyl-CoA condensations, the stilbene synthase (STS) from Pinus sylvestris forms the previously unknown pentaketide, 2-malonylresveratrol, in addition to the expected tetraketide resveratrol (see scheme). This is the first time that such tetra- and pentaketide-CoA derivatives have been observed; this suggests that these products might be free intermediates in the biosynthesis of stilbenes.<br /><br />The stilbene synthase (STS) from Scots pine (Pinus sylvestris), which is a type III polyketide synthase, produces the well known tetraketide resveratrol from coumaroyl-CoA and three molecules of malonyl-CoA. The same stilbene synthase, however, also generates the previously unknown pentaketide 2-malonylresveratrol from coumaroyl-CoA and four molecules of malonyl-CoA; this indicates that the enzyme does not precisely control the number of condensations leading to diverse products. Tetraketide- and pentaketide-CoA intermediates of the STS were identified by LC-MS/MS; this suggests that CoA-bound polyketide intermediates are involved in the product formation of type III polyketide synthases. Identification of a Pentaketide Stilbene Produced by a Type III Polyketide Synthase from Pinus sylvestris and Characterisation of Free Coenzyme A Intermediates Spiteller, Dieter Li, Tsung-Lin 2009-03-23 Spencer, Jonathan B. 2011-10-19T08:19:42Z

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