Beilstein Arch. 2025, 202541. https://doi.org/10.3762/bxiv.2025.41.v1
Published 25 Jun 2025
A 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).
Keywords: 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
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Suo, R.; Irie, R.; Nakayama, H.; Ishimaru, Y.; Akama, Y.; Oikawa, M.; Itoi, S. Beilstein Arch. 2025, 202541. doi:10.3762/bxiv.2025.41.v1
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