F13459, a new derivative of mycophenolic acid. II. Physico-chemical properties and structural elucidation

J Antibiot (Tokyo). 2001 Jun;54(6):494-500. doi: 10.7164/antibiotics.54.494.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemistry*
  • Chemical Phenomena
  • Chemistry, Physical
  • Magnetic Resonance Spectroscopy
  • Mycophenolic Acid / analogs & derivatives
  • Mycophenolic Acid / chemistry*
  • Penicillium / chemistry*
  • Spectrometry, Mass, Fast Atom Bombardment
  • Stereoisomerism

Substances

  • Antiviral Agents
  • F13459
  • Mycophenolic Acid