PMID: 2879564Dec 2, 1986

6-Thiocyanatoflavins and 6-mercaptoflavins as active-site probes of flavoproteins

Biochemistry
V MasseyK YAGI

Abstract

6-Thiocyanatoflavins have been found to be susceptible to nucleophilic displacement reactions with sulfite and thiols, yielding respectively the 6-S-SO3--flavin and 6-mercaptoflavin, with rate constants at pH 7.0, 20 degrees C, of 55 M-1 min-1 for sulfite and 1000 M-1 min-1 for dithiothreitol. The 6-SCN-flavin binds tightly to riboflavin-binding protein as the riboflavin derivative, to apoflavodoxin, apo-lactate oxidase, and apo-Old Yellow Enzyme as the FMN derivative, and to apo-D-amino acid oxidase as the FAD derivative. The riboflavin-binding protein derivative is inaccessible to dithiothreitol attack, and the lactate oxidase and D-amino acid oxidase derivatives show only limited accessibility. However, the flavodoxin and Old Yellow Enzyme derivatives react readily with dithiothreitol, indicating that the flavin 6-position is exposed to solvent in these proteins. The lactate oxidase and D-amino acid oxidase derivatives convert slowly but spontaneously to the 6-mercaptoflavin enzyme forms in the absence of any added thiol, indicating the presence of a thiol residue in the flavin binding site of these proteins. The reaction rates have been investigated of 6-mercaptoflavins with iodoacetamide, N-ethylmaleimide, methyl methaneth...Continue Reading

Citations

Nov 19, 2003·European Journal of Biochemistry·Marco H HeftiWillem J H van Berkel
Jul 1, 1997·Archives of Biochemistry and Biophysics·L PollegioniM S Pilone
Mar 20, 1990·Biochemistry·P MacherouxV Massey
Jan 15, 1991·Biochemistry·P Macheroux, V Massey
Feb 10, 1995·The Journal of Biological Chemistry·G TedeschiV Massey
Jun 7, 1996·The Journal of Biological Chemistry·L HuangR Hille

Related Concepts

Lactate 2-monooxygenase
6-thiocyanatoriboflavin
6-mercaptoriboflavin
D-Amino Acid Dehydrogenase
Flavins
Flavodoxin
Flavoproteins
Mixed Function Oxygenases
NADPH Dehydrogenase
Riboflavin

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