Abstract
The effect of the steric volume at C-19 of (3S)-2,3-oxidosqualene 1 on the polycyclization reaction by β-amyrin synthase was examined. The substrate analogs, in which the methyl group at C-19 of 1 was substituted by an ethyl group and hydrogen atom, were converted into the following three new compounds: (17β-H, 20S)-20-ethyl-dammara-12,24-diene 9, β-amyrin homologue 10, and the 6,6,6,6-fused tetracycle 11. The folding conformations leading to these products are discussed.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Cyclization
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Intramolecular Transferases / metabolism
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Molecular Conformation
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Oleanolic Acid / analogs & derivatives*
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Oleanolic Acid / biosynthesis
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Oleanolic Acid / chemistry
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Squalene / analogs & derivatives*
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Squalene / chemistry
Substances
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2,3-oxidosqualene
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oxidosqualene
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Oleanolic Acid
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Squalene
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Intramolecular Transferases
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2,3-oxidosqualene-beta-amyrin-cyclase
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beta-amyrin