Choi, Yukyung Kim, Yeongseo Cha, Jin Wook Lee, Gyu Sung Pham, Huong T. Ngo, Men Thi Kim, Saegun Kim, Chung Sub Kang, Kyo Bin 2025-01-20T01:30:43Z 2025-01-20T01:30:43Z 2025-01-17 2025-01 0163-3864 https://pubs.kist.re.kr/handle/201004/151596 Nonenzymatic reactions, though critical in natural product biosynthesis, are significantly challenging to control. Adding 3% NaI to the culture medium of Penicillium janczewskii significantly increased pseurotin D (1) production and decreased pseurotin A (2) production. Previously, 1 and 2 were suggested to be produced via a nonenzymatic reaction, where the epoxide at C-10 undergoes SN2 (2) or SN2 ' (1) reactions. We confirmed that 1 was isolated as a 1:1 mixture of C-13 epimers by spectral elucidation via CP3 analysis aided by selective excitation NMR methods, which supported that 1 was produced through a nonenzymatic SN2 ' reaction. We propose that NaI increased the ratio of 1 by causing steric hindrance at the C-11 position of the transient intermediate, which makes C-13 more preferred in the SN2/SN2 ' competition. English American Chemical Society Iodide Enhances the Production of Pseurotin D over Pseurotin A by Inverting the Preference for the SN2 versus the SN2′ Product in the Final Nonenzymatic Step Article 10.1021/acs.jnatprod.4c01128 1 Journal of Natural Products, v.88, no.1, pp.199 - 204 Journal of Natural Products 88 1 199 204 N scie scopus 001382209400001 2-s2.0-85213007404 Plant Sciences Chemistry, Medicinal Pharmacology & Pharmacy Plant Sciences Pharmacology & Pharmacy Article ELUCIDATION METABOLITES ALCOHOLS