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
References
Mar 9, 1976·Biochemistry·R SpencerC Walsh
Apr 1, 1976·European Journal of Biochemistry·S Ghisla, S G Mayhew
Jul 26, 1977·Biochemistry·S Quay, V Massey
May 16, 1978·Biochemistry·C WalshE F Rogers
Sep 28, 1977·Journal of the American Chemical Society·T C BruiceM Novak
Oct 26, 1977·Journal of the American Chemical Society·C KemalR C Bruice
Oct 1, 1986·The Biochemical Journal·S Ghisla, V Massey
Oct 1, 1967·European Journal of Biochemistry·A EhrenbergP Hemmerich
Oct 1, 1966·Biochemistry·V Massey, G Palmer
May 12, 1971·Biochimica Et Biophysica Acta·S G Mayhew
May 12, 1971·Biochimica Et Biophysica Acta·S G Mayhew
Aug 1, 1968·Biochemistry·D W Miles, D W Urry
Oct 1, 1967·The Journal of Organic Chemistry·K H Dudley, P Hemmerich
Feb 1, 1983·Journal of Biochemistry·S KasaiK Matsui
Feb 3, 1995·The Journal of Biological Chemistry·Y S NiinoV Massey
Oct 25, 1994·Biochemistry·A A Raibekas, M S Jorns
Oct 25, 1994·Biochemistry·A A Raibekas, M S Jorns
Apr 27, 1993·Biochemistry·A A RaibekasM S Jorns
Jan 29, 1962·Biochimica Et Biophysica Acta·K YAGI, T OZAWA
Jun 1, 1950·The Biochemical Journal·G WEBER
Citations
Sep 29, 2012·Organic Letters·Shuai Chen, Frank W Foss
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
Jul 6, 2000·The Journal of Biological Chemistry·R K Nandigama, D E Edmondson
Dec 4, 2019·Nature Chemistry·Michael J BlackTodd K Hyster
Feb 13, 1999·The Journal of Biological Chemistry·C M HarrisV 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
May 14, 2009·Biochemistry·Zachary T CampbellThomas O Baldwin
Jul 31, 2009·The Journal of Physical Chemistry. a·Susanne SalzmannWolfgang Gärtner
Jul 12, 2007·Chemical Reviews·Feyissa Gadissa Gelalcha
Nov 17, 2021·The Journal of Physical Chemistry. B·Rajiv K KarAnne-Frances Miller