Catalysis of phosphodiester transesterification by Cu(II)-terpyridine complexes with peripheral pendent base groups

Implications for the mechanism

Shanghao Liu, Andrew Hamilton

Research output: Contribution to journalArticle

Abstract

In this paper we show that in phosphodiester transesterification catalyzed by copper(II)-terpyridine complexes both the metal-bound hydroxyl group and the peripheral pendent tertiary amino groups can provide general base catalysis. At neutral pH the pendent amino groups dominate the process because the metal-bound hydroxyl group is protonated. However, the metal-bound hydroxyl group is more effective at high pH, probably due to its higher basicity and/or closer location to the bound substrate.

Original languageEnglish (US)
Pages (from-to)1107-1110
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number7
DOIs
StatePublished - Feb 17 1997

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Transesterification
Catalysis
Hydroxyl Radical
Metals
Group Processes
Coordination Complexes
Alkalinity
Copper
Substrates

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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abstract = "In this paper we show that in phosphodiester transesterification catalyzed by copper(II)-terpyridine complexes both the metal-bound hydroxyl group and the peripheral pendent tertiary amino groups can provide general base catalysis. At neutral pH the pendent amino groups dominate the process because the metal-bound hydroxyl group is protonated. However, the metal-bound hydroxyl group is more effective at high pH, probably due to its higher basicity and/or closer location to the bound substrate.",
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