Structural revision and absolute configuration of lateritin |
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| Authors: | Antonius RB Ola Amal H Aly Wenhan Lin Victor Wray Abdessamad Debbab |
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| Institution: | 1. Institute of Pharmaceutical Biology and Biotechnology, Heinrich Heine University Duesseldorf, Universitaetsstrasse 1, Geb. 26.23, 40225 Duesseldorf, Germany;2. State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, PR China;3. Helmholtz Centre for Infection Research, D-38124 Braunschweig, Germany;4. Department of Chemistry, Faculty of Science and Engineering, Nusa Cendana University, Jalan Adisucipto Penfui, 85001 Kupang, Indonesia |
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| Abstract: | ‘Lateritin’ (1), a morpholine-2,5-dione (depsipeptide), was reinvestigated for its structure and absolute configuration. On the basis of thorough 1D and 2D NMR and mass spectrometrical analyses, the structure of 1 was revised to be identical with beauvericin (8) and confirmed that beauvericin (8) is the trimeric lactone of ‘lateritin’ (1). The absolute configuration was determined by acidic hydrolysis, followed by application of Marfey’s method, menthyl ester derivatization, and GC–MS analysis. In addition, the specific optical rotation values of the hydrolysis products were compared with those of available standards. |
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| Keywords: | Absolute configuration Fusarium equiseti Lateritin Structural revision |
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