Synthesis and properties of 8-CN-flavin nucleotide analogs and studies with flavoproteins.

The Journal of Biological Chemistry
Y V Murthy, V Massey

Abstract

A high potential analog of riboflavin with a cyano function at the 8-position was synthesized by employing novel reaction conditions, starting from 8-amino-riboflavin. This was converted to the FAD level with FAD synthetase. The reduced 8-CN-riboflavin, unlike normal reduced flavin, has a distinctive absorption spectrum with two distinctive peaks in the near ultraviolet region. The oxidation-reduction potential of the new flavin was determined to be -50 mV, approximately 160 mV more positive than that of normal riboflavin. The 8-CN-riboflavin and 8-CN-FMN were found to be photoreactive and need to be protected from exposure to light. However such complications were not encountered with protein-bound flavins. The apoproteins of flavodoxin and Old Yellow Enzyme (OYE) were reconstituted with the 8-CN-FMN and apoDAAO was reconstituted with 8-CN-FAD. Spectral properties of the enzyme-bound neutral and anionic semiquinones were determined from these reconstituted proteins. In the case of 8-CN-FMN-OYE I, it was shown that the comproportionation reaction of a mixture of reduced and oxidized enzyme bound flavin is very rapid, compared with the same reaction with native protein, resulting in approximately 100% thermodynamically stable an...Continue Reading

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Citations

Apr 2, 2013·Journal of Biochemistry·Kyosuke SatoKiyoshi Shiga
Mar 31, 1999·Proceedings of the National Academy of Sciences of the United States of America·D XuV Massey
Mar 5, 2013·Chembiochem : a European Journal of Chemical Biology·Madina MansurovaWolfgang Gärtner
Dec 16, 2020·The Journal of Chemical Physics·Clare F MegarityFraser A Armstrong
Jul 12, 2007·Chemical Reviews·Feyissa Gadissa Gelalcha
Nov 17, 2021·The Journal of Physical Chemistry. B·Rajiv K KarAnne-Frances Miller

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