ArticlePhytochemistry2015
Characterization, mutagenesis and mechanistic analysis of an ancient algal sterol C24-methyltransferase: Implications for understanding sterol evolution in the green lineage.
Article in Phytochemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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15 citing papers in PubMed, 39 citations in OpenAlex.
- Non-enzymatic methylcyclization of alkenes.Nature chemistry · 2025Article
- Brassinosteroid biosynthesis and signaling: Conserved and diversified functions of core genes across multiple plant species.Plant communications · 2024Review
- Druggable Sterol Metabolizing Enzymes in Infectious Diseases: Cell Targets to Therapeutic Leads.Biomolecules · 2024Review
- De novo phytosterol synthesis in animals.Science (New York, N.Y.) · 2023Article
- Advances in steroidal saponins biosynthesis.Planta · 2021Review
- Sterol Biosynthesis in Four Green Algae: A Bioinformatic Analysis of the Ergosterol Versus Phytosterol Decision Point.Journal of phycology · 2021Article
- Inhibition of Phytosterol Biosynthesis by Azasterols.Molecules (Basel, Switzerland) · 2020Article
- Inferring Biochemical Reactions and Metabolite Structures to Understand Metabolic Pathway Drift.iScience · 2020Article
- A nematode sterol C4α-methyltransferase catalyzes a new methylation reaction responsible for sterol diversity.Journal of lipid research · 2020Article
- Steroidal antibiotics are antimetabolites of Acanthamoeba steroidogenesis with phylogenetic implications.Journal of lipid research · 2019Article
- Microbial Sterolomics as a Chemical Biology Tool.Molecules (Basel, Switzerland) · 2018Review
- Functional importance for developmental regulation of sterol biosynthesis in Acanthamoeba castellanii.Biochimica et biophysica acta. Molecular and cell biology of lipids · 2018Article
- Sterol methyltransferase a target for anti-amoeba therapy: towards transition state analog and suicide substrate drug design.Journal of lipid research · 2017Article
- Inhibition of Cycloartenol Synthase (CAS) Function in Tobacco BY-2 Cell Suspensions: A Proteomic Analysis.Lipids · 2015Article
- Article
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Authors and funding
9 authors at 2 institutions in 1 country.
Funding
Abstract
Sterol C24-methyltransferases (SMTs) constitute a group of sequence-related proteins that catalyze the pattern of sterol diversity across eukaryotic kingdoms. The only gene for sterol alkylation in green algae was identified and the corresponding catalyst from Chlamydomonas reinhardtii (Cr) was characterized kinetically and for product distributions. The properties of CrSMT were similar to those predicted for an ancient SMT expected to possess broad C3-anchoring requirements for substrate binding and formation of 24β-methyl/ethyl Δ(25(27))-olefin products typical of primitive organisms. Unnatural Δ(24(25))-sterol substrates, missing a C4β-angular methyl group involved with binding orientation, convert to product ratios in favor of Δ(24(28))-products. Remodeling the active site to alter the electronics of Try110 (to Leu) results in delayed timing of the hydride migration from methyl attack of the Δ(24)-bond, that thereby produces metabolic switching of product ratios in favor of Δ(25(27))-olefins or impairs the second C1-transfer activity. Incubation of [27-(13)C]lanosterol or [methyl-(2)H3]SAM as co-substrates established the CrSMT catalyzes a sterol methylation pathway by the "algal" Δ(25(27))-olefin route, where methylation proceeds by a conserved SN2 reaction and de-protonation proceeds from the pro-Z methyl group on lanosterol corresponding to C27. This previously unrecognized catalytic competence for an enzyme of sterol biosynthesis, together with phylogenomic analyses, suggest that mutational divergence of a promiscuous SMT produced substrate- and phyla-specific SMT1 (catalyzes first biomethylation) and SMT2 (catalyzes second biomethylation) isoforms in red and green algae, respectively, and in the case of SMT2 selection afforded modification in reaction channeling necessary for the switch in ergosterol (24β-methyl) biosynthesis to stigmasterol (24α-ethyl) biosynthesis during the course of land plant evolution.
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