{"paper_id":"2f7438c8-b9b1-4aec-859b-b2467daa1db9","body_text":"Submitting author affiliation:\nNihon University, Fujisawa, Japan\nBeilstein Arch. 2025, 202541. https://doi.org/10.3762/bxiv.2025.41.v1\nPublished 25 Jun 2025\nRead the peer-reviewed version of this preprint:\nhttps://doi.org/10.3762/bjoc.21.171\nShow All Preprints\nNanotechnology\nOrganic chemistry\nBioorganic chemistry / chemical biology\nCatalysis\nChemical methods and reactions\nFlow and process chemistry\nGreen and sustainable chemistry\nMaterials chemistry\nMedicinal and pharmaceutical chemistry\nNano- and molecular-scale electronics\nNano-biomaterials and bioscience\nNanomagnetics\nNanomaterials, thin films and nanointerfaces\nNanomedicine\nNanometrology and nanomechanics\nNano-optics\nNanopatterning, self-assembly and nanofabrication\nNanostructures for energy and sensing applications\nNatural products chemistry\nOrgano main group chemistry\nOther nanotechnology (unclassified)\nOther organic chemistry (unclassified)\nPhotochemistry and photovoltaics\nPhysical organic chemistry\nSupramolecular chemistry\nA terminal 3-methylpent-4-en-2-ol (MPO) moiety is a common structural feature in various polyketide natural products. Stereochemical assignments of this moiety have mainly relied on computational analyses of NMR, ECD, and specific rotation data. However, neither of these approaches can be applied to all compounds. In this study, we developed an accurate and sensitive method to determine the absolute configuration of the terminal MPO moiety by a combination of chemical degradation, chemical synthesis, and chiral LC-MS analysis. The applicability of this method was demonstrated through the stereochemical assignment of capsulactone (1).\nKeywords: a terminal 3-methylpent-4-en-2-ol (MPO) moiety; p-nitrobenzoyl (PNB) ester; methyl-3-hydroxy-2-methylbutanoate; chemical degradation; chiral LC-MS analysis\n| Format: PDF | Size: 1.6 MB | Download |\nWhen a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:\nSuo, R.; Irie, R.; Nakayama, H.; Ishimaru, Y.; Akama, Y.; Oikawa, M.; Itoi, S. Beilstein Arch. 2025, 202541. doi:10.3762/bxiv.2025.41.v1\nCitation data can be downloaded as file using the \"Download\" button or used for copy/paste from the text window below.\nCitation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and\nZotero.\n© 2025 Suo et al.; licensee Beilstein-Institut.\nThis is an open access work licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-archives.org/xiv/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this work could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.","source_license":"CC-BY-4.0","license_restricted":false}