کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1317093 | 1499481 | 2007 | 6 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
Insights into the nature of the hydrogen bonding of Tyr272 in apo-galactose oxidase
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کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی معدنی
پیش نمایش صفحه اول مقاله
چکیده انگلیسی
The synthesis and structure of an o-methylthio-phenol-imidazole, 2-(2â²-(4â²-tert-butyl-6â²-methylsulfanyl)-hydroxyphenyl))-4,5-diphenyl-imidazole (MeSLH), is reported; X-ray crystallographic studies have shown that MeSLH involves an O-H···N+ hydrogen bond between the phenol and an imidazole nitrogen. MeSLH undergoes a reversible, one-electron, oxidation to form the radical cation [MeSLH]+ the EPR spectrum of which is remarkably similar to that of Tyr272 in Cu-free, oxidized, apo-GO. Density Functional Theory calculations, have shown that the proton-transferred (R-O···H-N+) form of [MeSLH]+ has a spin density distribution - with a substantial delocalization of the unpaired electron spin density onto the ortho sulfur atom - and EPR properties that are in good agreement with those of Tyr272 in Cu-free, oxidized, apo-GO whereas the non-proton-transferred (R-O+-H···N) form does not. The results reported herein are a further demonstration of the influence of hydrogen bonding on the nature and properties of phenoxyl radicals and strongly suggest that the phenoxyl oxygen of Tyr272 in Cu-free, oxidized, apo-GO is involved in a O···H-O/N hydrogen bond.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Journal of Inorganic Biochemistry - Volume 101, Issues 11â12, November 2007, Pages 1859-1864
Journal: Journal of Inorganic Biochemistry - Volume 101, Issues 11â12, November 2007, Pages 1859-1864
نویسندگان
Laurent Benisvy, Deborah Hammond, David J. Parker, E. Stephen Davies, C. David Garner, Jonathan McMaster, Claire Wilson, Frank Neese, Eberhard Bothe, Robert Bittl, Christian Teutloff,