F13459, a New Derivative of Mycophenolic Acid. II. Physico-chemical Properties and Structural Elucidation.
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- KOSHINO HIROYUKI
- Molecular Characterization Division, Characterization Center
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- MUROI MAKOTO
- Animal and Cellular Systems Laboratory, RIKEN (The Institute of Physical and Chemical Research)
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- TAJIKA TATSUHARU
- Molecular Characterization Division, Characterization Center
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- KIMURA YASUO
- Department of Agricultural Chemistry, Faculty of Agriculture, Tottori University
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- TAKATSUKI AKITA
- Animal and Cellular Systems Laboratory, RIKEN (The Institute of Physical and Chemical Research)
書誌事項
- タイトル別名
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- II. Physico-chemical Properties and Structural Elucidation
抄録
F13459 is a new inhibitor of synthesis and trafficking of virus glycoprotein isolated from the culture broth of a Penicillium sp. The molecular formula of F13459 was determined to be C27H28O11 by HRFAB-MS and NMR spectral analyses. The structure of F13459 was elucidated to be 3, 4-dihydro-3, 4., 6, 84etrahydroxy-3-methyl-1H-2-benzopyran-1-one 4-O-mycophenolate, an ester derivative of mycophenolic acid. F13459 was isolated as the optically inactive form. F13459 exists in epimeric mixtures at C-3' through relatively fast hemiacetal-ketone tautomerism and at C-4' through slow keto-enol tautomerism. Those epimerizations were confirmed by NOE differential experiments for fast chemical exchange and equilibrium and by deuteration experiments in NMR for slow chemical exchange.
収録刊行物
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- The Journal of Antibiotics
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The Journal of Antibiotics 54 (6), 494-500, 2001
公益財団法人 日本感染症医薬品協会
