Synthetic hydrogen bonding receptors as models of transacylase enzymes

Paolo Tecilla, Vrej Jubian, Andrew Hamilton

Research output: Contribution to journalArticle

Abstract

A family of synthetic receptors has been prepared containing a barbiturate binding site and an appended thiol nucleophile. These are shown to cause large accelerations in the thiolysis reactions of barbiturate active ester derivatives. The size of the acceleration is shown to depend critically on the length and flexibility of the spacer that links the thiol to the receptor.

Original languageEnglish (US)
Pages (from-to)435-448
Number of pages14
JournalTetrahedron
Volume51
Issue number2
DOIs
StatePublished - Jan 9 1995

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Hydrogen Bonding
Sulfhydryl Compounds
Hydrogen bonds
Artificial Receptors
Nucleophiles
Enzymes
Esters
Binding Sites
Derivatives
barbituric acid

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthetic hydrogen bonding receptors as models of transacylase enzymes. / Tecilla, Paolo; Jubian, Vrej; Hamilton, Andrew.

In: Tetrahedron, Vol. 51, No. 2, 09.01.1995, p. 435-448.

Research output: Contribution to journalArticle

Tecilla, Paolo ; Jubian, Vrej ; Hamilton, Andrew. / Synthetic hydrogen bonding receptors as models of transacylase enzymes. In: Tetrahedron. 1995 ; Vol. 51, No. 2. pp. 435-448.
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