Hydrolytic enzymatic transformation of advanced synthetic intermediates: On the choice of the organic cosolvent

David B. Berkowitz, Ryan E. Hartung, Sungjo Choi

Research output: Contribution to journalArticle

12 Scopus citations

Abstract

For enzymatic hydrolyses of advanced synthetic intermediates, the use of an organic cosolvent is often warranted. As a model study, the cosolvent dependence (at 10 volume%) of the key enzymatic step in our asymmetric synthesis of (-)-podophyllotoxin was examined. At high protein concentrations and rt, DMSO and the polyethereal organic cosolvents dioxane, diglyme and triglyme emerged as the best organic cosolvents, in terms of yield, % ee and catalytic efficiency (V(max)/K(m)). However, only in 10% triglyme was optimal efficiency maintained at both lower protein concentration and higher temperature. (C) 1999 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)4513-4520
Number of pages8
JournalTetrahedron Asymmetry
Volume10
Issue number23
DOIs
StatePublished - Dec 3 1999

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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