Stereochemical aspects of cytosolic epoxide hydrolase hydration of methyl diepoxystearates

Babak Borhan, Jaffar Nourooz-Zadeh, Tamon Uematsu, Bruce D. Hammock, Mark J. Kurth

Research output: Contribution to journalArticlepeer-review

15 Scopus citations


Hydration of methyl diepoxystearate (2) at high cytosolic epoxide hydrolase (CEH) concentration produces the corresponding tetraol, while at physiological CEH concentration four tetrahydrofuran diol products (3-6) are produced. These same four products are obtained in the acid-catalyzed hydration of 2. Spectroscopic studies, primarily EI mass spectrometry and difference spectrum NOE, are reported which establish the regio- and stereoselectivity of 2 → 3-6 (MS differentiating 3 4 from 5 6 and NOE differentiating 3 5 from 4 6). The observed syn arrangement of the two adjacent groups (i.e., substituents at C2 and C3) in the four THF-diols can only arise from an A2 type opening of the first epoxide. The resulting epoxydiol intermediate then cyclizes by A2 opening of the second cis-epoxide as established by synthesis of these hypothetical epoxydiol intermediates and their subsequent conversion to THF-diols 3-6.

Original languageEnglish (US)
Pages (from-to)2601-2612
Number of pages12
Issue number13
StatePublished - Mar 26 1993

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery


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