F13459, a New Derivative of Mycophenolic Acid: II. Physico-chemical Properties and Structural Elucidation

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,...

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Bibliographic Details
Published in:Journal of antibiotics 2001/06/25, Vol.54(6), pp.494-500
Main Authors: KOSHINO, HIROYUKI, MUROI, MAKOTO, TAJIKA, TATSUHARU, KIMURA, YASUO, TAKATSUKI, AKITA
Format: Article
Language:English
Subjects:
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antiviral agents
Antiviral Agents - chemistry
Biological and medical sciences
Chemical Phenomena
Chemistry, Physical
Magnetic Resonance Spectroscopy
Medical sciences
Mycophenolic Acid - analogs & derivatives
Mycophenolic Acid - chemistry
Penicillium - chemistry
Pharmacology. Drug treatments
Spectrometry, Mass, Fast Atom Bombardment
Stereoisomerism
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Summary: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.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.54.494