ArticlePlant physiology2014
Determination of residues responsible for substrate and product specificity of Solanum habrochaites short-chain cis-prenyltransferases.
Article in Plant physiology, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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20 citing papers in PubMed, 39 citations in OpenAlex.
- Specific residues and conformational plasticity define the substrate specificity of short-chain dehydrogenases/reductases.The Journal of biological chemistry · 2024Article
- Complexation and evolution of cis-prenyltransferase homologues in Cinnamomum kanehirae deduced from kinetic and functional characterizations.Protein science : a publication of the Protein Society · 2023Article
- Genetic and physiological requirements for high-level sesquiterpene-production in tomato glandular trichomes.Frontiers in plant science · 2023Article
- Fruity, sticky, stinky, spicy, bitter, addictive, and deadly: evolutionary signatures of metabolic complexity in the Solanaceae.Natural product reports · 2022Review
- Biosynthesis of (Engineering in life sciences · 2022Article
- Article
- Ancestral sequence reconstruction - An underused approach to understand the evolution of gene function in plants?Computational and structural biotechnology journal · 2021Review
- Harnessing evolutionary diversification of primary metabolism for plant synthetic biology.The Journal of biological chemistry · 2019Review
- Isoprenyl diphosphate synthases: the chain length determining step in terpene biosynthesis.Planta · 2019Review
- Characterization of Trichome-Expressed BAHD Acyltransferases inPlant physiology · 2017Article
- Article
- cis-Prenyltransferase: New Insights into Protein Glycosylation, Rubber Synthesis, and Human Diseases.The Journal of biological chemistry · 2016Review
- Evolutionarily Distinct BAHD N-Acyltransferases Are Responsible for Natural Variation of Aromatic Amine Conjugates in Rice.The Plant cell · 2016Article
- Biotechnological production of limonene in microorganisms.Applied microbiology and biotechnology · 2016Review
- In vitro reconstruction and analysis of evolutionary variation of the tomato acylsucrose metabolic network.Proceedings of the National Academy of Sciences of the United States of America · 2016Article
- Integrative Approaches to Enhance Understanding of Plant Metabolic Pathway Structure and Regulation.Plant physiology · 2015Article
- Article
- Biosynthesis of the diterpenoid lycosantalonol via nerylneryl diphosphate in Solanum lycopersicum.PloS one · 2015Article
- A root-expressed L-phenylalanine:4-hydroxyphenylpyruvate aminotransferase is required for tropane alkaloid biosynthesis in Atropa belladonna.The Plant cell · 2014Article
- A versatile cis-prenyltransferase from Methanosarcina mazei catalyzes both C- and O-prenylations.The Journal of biological chemistryArticle
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5 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Isoprenoids are diverse compounds that have their biosynthetic origin in the initial condensation of isopentenyl diphosphate and dimethylallyl diphosphate to form C10 prenyl diphosphates that can be elongated by the addition of subsequent isopentenyl diphosphate units. These reactions are catalyzed by either cis-prenyltransferases (CPTs) or trans-prenyltransferases. The synthesis of volatile terpenes in plants typically proceeds through either geranyl diphosphate (C10) or trans-farnesyl diphosphate (C15), to yield monoterpenes and sesquiterpenes, respectively. However, terpene biosynthesis in glandular trichomes of tomato (Solanum lycopersicum) and related wild relatives also occurs via the cis-substrates neryl diphosphate (NPP) and 2Z,6Z-farnesyl diphosphate (Z,Z-FPP). NPP and Z,Z-FPP are synthesized by neryl diphosphate synthase1 (NDPS1) and Z,Z-farnesyl diphosphate synthase (zFPS), which are encoded by the orthologous CPT1 locus in tomato and Solanum habrochaites, respectively. In this study, comparative sequence analysis of NDPS1 and zFPS enzymes from S. habrochaites accessions that synthesize either monoterpenes or sesquiterpenes was performed to identify amino acid residues that correlate with the ability to synthesize NPP or Z,Z-FPP. Subsequent structural modeling, coupled with site-directed mutagenesis, highlighted the importance of four amino acids located within conserved domain II of CPT enzymes that form part of the second α-helix, for determining substrate and product specificity of these enzymes. In particular, the relative positioning of aromatic amino acid residues at positions 100 and 107 determines the ability of these enzymes to synthesize NPP or Z,Z-FPP. This study provides insight into the biochemical evolution of terpene biosynthesis in the glandular trichomes of Solanum species.
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