ArticleThe Biochemical journal2000
Identification of amino acid residues important in the cyclization reactions of chalcone and stilbene synthases.
Article in The Biochemical journal, 2000. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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Who cites it
28 citing papers in PubMed, 88 citations in OpenAlex.
- A case study of evolutionary variability and determinism among type III polyketide synthases.Nature communications · 2026Article
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- Total Flavonoid Contents and the Expression of Flavonoid Biosynthetic Genes in Breadfruit (Plants (Basel, Switzerland) · 2023Article
- Characterization of the Key Bibenzyl Synthase inInternational journal of molecular sciences · 2022Article
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- Identification and Characterization of Flavonoid Biosynthetic Enzyme Genes in Salvia miltiorrhiza (Lamiaceae).Molecules (Basel, Switzerland) · 2018Article
- Functional Promiscuity of Two Divergent Paralogs of Type III Plant Polyketide Synthases.Plant physiology · 2016Article
- Type III polyketide synthase repertoire in Zingiberaceae: computational insights into the sequence, structure and evolution.Development genes and evolution · 2016Article
- Toward the Reconstitution of a Two-Enzyme Cascade for Resveratrol Synthesis on Potyvirus Particles.Frontiers in plant science · 2016Article
- Phylogeny and Expression Analyses Reveal Important Roles for Plant PKS III Family during the Conquest of Land by Plants and Angiosperm Diversification.Frontiers in plant science · 2016Article
- Chalcone synthase genes from milk thistle (Silybum marianum): isolation and expression analysis.Journal of genetics · 2015Article
- Functional characterization of a chalcone synthase from the liverwort Plagiochasma appendiculatum.Plant cell reports · 2015Article
- Crystal structure of Mycobacterium tuberculosis polyketide synthase 11 (PKS11) reveals intermediates in the synthesis of methyl-branched alkylpyrones.The Journal of biological chemistry · 2013Article
- Physcomitrella PpORS, basal to plant type III polyketide synthases in phylogenetic trees, is a very long chain 2'-oxoalkylresorcinol synthase.The Journal of biological chemistry · 2013Article
- Enzymatic properties and mutational studies of chalcone synthase from Physcomitrella patens.International journal of molecular sciences · 2012Article
- 3-Hydroxy-2-[(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)(thiophen-3-yl)methyl]-5,5-dimethylcyclohex-2-en-1-one.Acta crystallographica. Section E, Structure reports online · 2011Article
- High-yield resveratrol production in engineered Escherichia coli.Applied and environmental microbiology · 2011Article
- Evolutionary Implications and Physicochemical Analyses of Selected Proteins of Type III Polyketide Synthase Family.Evolutionary bioinformatics online · 2011Article
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Authors and funding
7 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Chalcone synthase (CHS) and stilbene synthase (STS) catalyse condensation reactions of p-coumaroyl-CoA and three C(2) units from malonyl-CoA up to a common tetraketide intermediate but then catalyse different cyclization reactions to produce naringenin chalcone and resveratrol respectively. On the basis of sequence alignment with other condensing enzymes including 3-ketoacyl-(acyl carrier protein) synthases of polyketide and fatty-acid synthases, site-directed mutagenesis was performed on the active-site G(372)FGPG loops in CHS and STS. The CHS-P375G mutant showed a 6-fold decrease in overall condensing activity with selectively increased production of p-coumaroyltriacetic acid lactone (CTAL, the derailment product of the tetraketide intermediate). Meanwhile, resveratrol production by STS-P(375)G strongly decreased to give various products in the order CTAL> resveratrol approximately bisnoryangonin>naringenin. As a result, naringenin production (cross-reaction) by STS-P(375)G was close to 30% of resveratrol production. Both G(374)L mutants of CHS and STS showed no condensing activity with residual malonyl-CoA decarboxylase activity. These results suggested that the G(372)FGPG loop in CHS and STS contribute to a determination of the outcome during cyclization reactions by serving as a part of the active-site scaffold on which the stereochemistry of cyclization is performed. These observations provide the first biochemical indication that cyclization reactions are modulated by active-site geometry. The implications for the evolutionary relationship of these enzymes are also discussed.
Indexed as
Identifiers
10926848PMC1221246W2139846328What OpenQuestion holds
Registered trials
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