Department of Bioorganic Chemistry, Max Planck Institute for Chemical Ecology, Hans-Knöll Straße 8, D-07745 Jena, Germany.
Laboratory for Bioanalytical Chemistry, Institute of Chemistry, University of Neuchâtel, Avenue de Bellevaux 51, CH-2000 Neuchâtel, Switzerland.
Org Biomol Chem. 2020 Jul 15;18(27):5253-5263. doi: 10.1039/d0ob00799d.
Comparative ascaroside profiling of Caenorhabditis nematodes using HPLC-ESI-(-)-MS/MS precursor ion scanning revealed a class of highly species-specific ascaroside dimers. Their 2- and 4-isomeric, homo- and heterodimeric structures were identified using a combination of HPLC-ESI-(+)-HR-MS/MS spectrometry and high-resolution dqf-COSY NMR spectroscopy. Structure assignments were confirmed by total synthesis of representative examples. Functional characterization using holding assays indicated that males of Caenorhabditis remanei and Caenorhabditis nigoni are exclusively retained by their conspecific ascaroside dimers, demonstrating that dimerization of conserved monomeric building blocks represents a yet undescribed mechanism that generates species-specific signaling molecules in the Caenorhabditis genus.
使用 HPLC-ESI-(-)-MS/MS 前体离子扫描对秀丽隐杆线虫进行比较ascaroside 分析，揭示了一类高度种特异性的ascaroside 二聚体。使用 HPLC-ESI-(+)-HR-MS/MS 光谱法和高分辨率 dqf-COSY NMR 光谱法相结合，鉴定了它们的 2-和 4-异构体、同型和异型二聚体结构。通过代表性实例的全合成验证了结构分配。使用保持测定的功能表征表明，Caenorhabditis remanei 和 Caenorhabditis nigoni 的雄性仅被其同种 ascroside 二聚体保留，这表明保守单体构建块的二聚化代表了一种尚未描述的机制，该机制在秀丽隐杆线虫属中产生种特异性信号分子。
