TY - JOUR
T1 - A relationship between amide hydrogen bond strength and quinone reduction potential
T2 - Implications for photosystem I and bacterial reaction center quinone function
AU - Feldman, Ken S.
AU - Hester, D. Keith
AU - Golbeck, John H.
N1 - Funding Information:
Funding via the National Institutes of Health, General Medical Sciences Division (GM 37681) and the Molecular Biochemistry/Biophysics Program of the National Science Foundation (MCB-0519743) is gratefully acknowledged. In addition, the National Science Foundation is acknowledged for the X-Ray structural analysis facility (CHE-013111).
PY - 2007/9/1
Y1 - 2007/9/1
N2 - 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.
AB - 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.
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U2 - 10.1016/j.bmcl.2007.06.041
DO - 10.1016/j.bmcl.2007.06.041
M3 - Article
C2 - 17596943
AN - SCOPUS:34547514794
SN - 0960-894X
VL - 17
SP - 4891
EP - 4894
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
IS - 17
ER -