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-3,4,6,8-tetrahydroxy-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.
Koshino
H
H
Molecular Characterization Division, Characterization Center, Wako-shi, Saitama, Japan. koshino@postman.riken.go.jp
Muroi
M
M
Tajika
T
T
Kimura
Y
Y
Takatsuki
A
A
D000998:Antiviral Agents / Q000737:chemistry*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D009682:Magnetic Resonance Spectroscopy; D009173:Mycophenolic Acid / Q000031:analogs & derivatives / Q000737:chemistry*; D010407:Penicillium / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism
D000998:Antiviral Agents; C434148:F13459; D009173:Mycophenolic Acid