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


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.

SUBMITTER: Feldman KS 

PROVIDER: S-EPMC2084345 | biostudies-literature | 2007 Sep

REPOSITORIES: biostudies-literature

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

Feldman Ken S KS   Hester D Keith DK   Golbeck John H JH  

Bioorganic & medicinal chemistry letters 20070614 17


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 stro  ...[more]

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