Zhou, Wenxu; Fisher, Paxtyn M.; Vanderloop, Boden H.; Shen, Yun; Shi, Huazhong; Maldonado, Adrian J.; Leaver, David J.; Nes, W. David published the artcile< A nematode sterol C4α-methyltransferase catalyzes a new methylation reaction responsible for sterol diversity>, Application In Synthesis of 434-16-2, the main research area is C4alpha methyltransferase dinosterol Caenorhabditis review; 8(14)-lophenol; Caenorhabditis elegans • biosynthesis; evolution.
A review. Primitive sterol evolution plays an important role in fossil record interpretation and offers potential therapeutic avenues for human disease resulting from nematode infections. Recognizing that C4-Me stenol products [8(14)-lophenol] can be synthesized in bacteria while C4-Me stanol products (dinosterol) can be synthesized in dinoflagellates and preserved as sterane biomarkers in ancient sedimentary rock is key to eukaryotic sterol evolution. In this regard, nematodes have been proposed to convert dietary cholesterol to 8(14)-lophenol by a secondary metabolism pathway that could involve sterol C4 methylation analogous to the C2 methylation of hopanoids (radicle-type mechanism) or C24 methylation of sterols (carbocation-type mechanism). Here, we characterized dichotomous cholesterol metabolic pathways in Caenorhabditis elegans that generate 3-oxo sterol intermediates in sep. paths to lophanol (4-Me stanol) and 8(14)-lophenol (4-Me stenol). We uncovered alternate C3-sterol oxidation and Δ7 desaturation steps that regulate sterol flux from which branching metabolite networks arise, while lophanol/8(14)-lophenol formation is shown to be dependent on a sterol C4α-methyltransferse (4-SMT) that requires 3-oxo sterol substrates and catalyzes a newly discovered 3-keto-enol tautomerism mechanism linked to S-adenosyl-l-methionine-dependent methylation. Alignment-specific substrate-binding domains similarly conserved in 4-SMT and 24-SMT enzymes, despite minimal amino acid sequence identity, suggests divergence from a common, primordial ancestor in the evolution of Me sterols. The combination of these results provides evolutionary leads to sterol diversity and points to cryptic C4-Me steroidogenic pathways of targeted convergence that mediate lineage-specific adaptations.
Journal of Lipid Research published new progress about Caenorhabditis elegans. 434-16-2 belongs to class alcohols-buliding-blocks, and the molecular formula is C27H44O, Application In Synthesis of 434-16-2.
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts