A relationship between amide hydrogen bond strength and quinone reduction potential: Implications for photosystem I and bacterial reaction center quinone function

Ken S. Feldman, D. Keith Hester, John H. Golbeck

Research output: Contribution to journalArticle

17 Scopus citations

Abstract

A series of 11 simple phylloquinone derivatives, each lacking the extended phytyl side chain but featuring H-bond donor amides at one or both peri positions, were prepared and some salient physical properties were measured. A correlation between both IR frequency and NMR peak position, as indicators of internal H-bond strength, and the quinone half-wave reduction potential, was observed. These data are consistent with the prevailing hypothesis that quinone carbonyl H-bonding in general, and stronger H-bonds in particular, favorably bias the endogenous quinone's electrochemical potential toward easier reduction.

Original languageEnglish (US)
Pages (from-to)4891-4894
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume17
Issue number17
DOIs
StatePublished - Sep 1 2007

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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