A trail of research on cofactors: An odyssey with friends

Journal of Nutrition

Volumn 130, Issue 2 SUPPL., 2000, Pages

  McCormick, Donald B ^a  

^a EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Coenzymes; Cofactors; Divalent cations; Vitamin metabolism; Water soluble vitamins

Indexed keywords

ASCORBIC ACID; BIOTIN; DIVALENT CATION; FLAVINE ADENINE NUCLEOTIDE; FLAVOPROTEIN; OXIDOREDUCTASE; PYRIDOXINE; RIBOFLAVIN; RIBOFLAVIN KINASE; SYNTHETASE; THIOCTIC ACID; VITAMIN;

AFFINITY CHROMATOGRAPHY; CATALYSIS; COENZYME; CONFERENCE PAPER; DRUG ABSORPTION; DRUG EXCRETION; DRUG MECHANISM; NONHUMAN; VITAMIN METABOLISM;

EUKARYOTA; MAMMALIA;

EID: 0033960124     PISSN: 00223166     EISSN: None     Source Type: Journal    
DOI: 10.1093/jn/130.2.323s     Document Type: Conference Paper

References (203)

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100. McCormick, D. B., Bowers-Komro, D. M., Bonkovsky, J., Larson, C. & Zhang, Z. (1991) Characteristics of a transporter for uptake of vitamin B6 into mammalian cells: Isolation of B6 binding proteins from the brush-border membranes of rat renal proximal tubular epithelial cells. In: Enzymes Dependent on Pyridoxal Phosphate and Other Carbonyl Compounds as Cofactors (Fukui, T., Kagamiyama, H., Soda, K., & Wada, H., eds.) pp. 609-611, Pergamon Press, NY.
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102. McCormick, D. B., Chassy, B. M. & Tsibris, J.C.M. (1964) Coenzyme specificity of D-amino acid oxidase for the adenylate moiety of FAD. Biochim. Biophys. Acta 89: 447-452.
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105. McCormick, D. B., Gregory, M. E. & Snell, E. E. (1961) Pyridoxal phosphokinases. I. Assay, distribution, purification, and properties. J. Biol. Chem. 236: 2076-2084.
106. McCormick, D. B., Griesser, R. & Sigel, H. (1974) Metal ion-thioether interactions of biological interest. In: Metals Ions in Biological Systems (Sigel, H., ed.) Chap. 6 pp. 213-246. Marcel Dekker, NY.
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108. McCormick, D. B., Innis, W.S.A., Merrill, A. H., Jr., Bowers-Komro, D. M., Oka, M. & Chastain, J. L. (1988) An update on flavin metabolism in rats and humans. In: Flavins and Flavoproteins (Edmondson, D. E. and McCormick, D. B., eds.) pp. 459-471. Walter de Gruyter, NY.
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111. McCormick, D. B., Koster, J. F. & Veeger, C. (1967) On the mechanisms of photochemical reductions of FAD and FAD-dependent enzymes. Eur. J. Biochem. 2: 387-391.
112. McCormick, D. B., Li, H. C. & MacKenzie, R. E. (1967) Spectral evidence for the interaction of riboflavin with aromatic hydrocarbons. Spectrochim. Acta 23A: 2353-2358.
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116. McCormick, D. B. & Roth, J. A. (1970) Specificity, stereochemistry and mechanism of the color reaction between p-dimethylaminocinnamaldehyde and biotin analogues. Anal. Biochem. 34: 226-236.
117. McCormick, D. B. & Russell, M. (1962) Hydrolysis of flavin mononucleotide by acid phosphatases from animal tissues. Comp. Biochem. Physiol. 5: 113-121.
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123. 14C]arabitol to liver glycogen in the rat and guinea pig. Biochim. Biophys. Acta 192: 598-600.
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127. Merrill, A. H., Jr., Addison, R. & McCormick, D. B. (1978a) Induction of hepatic and intestinal flavokinase after oral administration of riboflavin to riboflavin-deficient rats. Proc. Soc. Exp. Biol. Med. 158: 572-574.
128. Merrill, A. H., Jr., Froehlich, J. A. & McCormick, D. B. (1979a) Purification of riboflavin-binding proteins from bovine plasma and discovery of a pregnancy-specific riboflavin-binding protein. J. Biol. Chem. 254: 9362-9364.
129. Merrill, A. H., Jr., Froehlich, J. A. & McCormick, D. B. (1981a) Isolation and identification of alternative riboflavin-binding proteins from human plasma. Biochem. Med. 25: 198-206.
130. Merrill, A. H., Jr., Horiike, K. & McCormick, D. B. (1978b) Evidence for the regulation of pyridoxal 5′-phosphate formation in liver by pyridoxamine (pyridoxine) 5′-phosphate oxidase. Biochem. Biophys. Res. Commun. 83: 984-990.
131. Merrill, A. H., Jr., Kasai, S., Matsui, K., Tsuge, H. & McCormick, D. B. (1979b) Spectroscopic studies of pyridoxamine (pyridoxine) 5′-phosphate oxidase. Equilibrium dissociation constants and spectra for riboflavin 5′-phosphate and analogs. Biochemistry 18: 3635-3641.
132. Merrill, A. H., Jr., Korytnyk, W., Horiike, K. & McCormick, D. B. (1980) Spectroscopic studies of complexes between pyridoxamine (pyridoxine) 5′-phosphate oxidase and pyridoxyl 5′-phosphate compounds differing at position 4′. Biochim. Biophys. Acta 626: 57-63.
133. Merrill, A. H., Jr., Lambeth, J. D., Edmondson, D. E. & McCormick, D. B. (1981b) Formation and mode of action of flavoproteins. In: Annual Review of Nutrition (Darby, W. J., ed.) Vol. 1, Chap. 12, pp. 281-317. Annual Reviews, Inc., Palo Alto, CA.
134. Merrill, A. H., Jr. & McCormick, D. B. (1978) Flavin affinity chromatography: General methods for purification or proteins that bind riboflavin. Anal. Biochem. 89: 87-102.
135. Merrill, A. H., Jr. & McCormick, D. B. (1979) Preparation and properties of immobilized flavokinase. Biotechnol. Bioeng. XXI: 243-252.
136. Merrill, A. H., Jr. & McCormick, D. B. (1980) Affinity chromatographic purification and properties of flavokinase (ATP: Riboflavin 5′-phosphotransferase) from rat liver. J. Biol. Chem. 255: 1335-1338.
137. Merrill, A. H., Jr., Shapira, G. & McCormick, D. B. (1982) Recent findings concerning mammalian riboflavin-binding proteins. In: Flavins and Flavoproteins (Massey, V. and Williams, C. H., Jr., eds.) pp. 508-513. Elsevier Biomedical, NY.
138. Nakano, H., Hartman, H. & McCormick, D. B. (1992) Mammalian flavokinase and FAD synthetase: Functions of divalent metal ions and arginyl residues in the anionic substrate sites. In: 1st Internat'l. Congress on Vitamins and Biofactors in Life Science (Kobayashi, T., ed.) pp. 450-452, Center for Academic Publications, Osaka, Japan.
139. Nakano, H. & McCormick, D. B. (1991a) Rat brain flavokinase: purification, properties, and comparison to the enzyme from liver and small intestine. In: Flavins and Flavoproteins 1990 (Curti, B., Ronchi, S. & Zanetti, G., eds.) pp. 89-92, Walter de Gruyter, NY.
140. Nakano, H. & McCormick, D. B. (1991b) Stereospecificity of the Metal. ATP complex in flavokinase from rat small intestine. J. Biol. Chem. 266: 22125-22128.
141. Nakano, H. & McCormick, D. B. (1992) Modification of arginyl and lysyl residues in flavokinase from rat small intestine. Biochem. Internatl. 28 (No. 3): 441-450.
142. Ogunmodede, B. K. & McCormick, D. B. (1966) Sparing of riboflavin in rats by 6,7-dimethyl-9-(ω-hydroxyalkyl) isoalloxazines. Proc. Soc. Exp. Biol. Med. 122: 845-847.
143. Oka, M. & McCormick, D. B. (1985) Urinary lumichrome-level catabolites of riboflavin are due to microbial and photochemical events and not tissue enzymic cleavage of the ribityl chain. J. Nutr. 115: 496-499.
144. Oka, M. & McCormick, D. B. (1987) Complete purification and general characterization of FAD synthetase from rat liver. J. Biol. Chem. 262: 7418-7422.
145. Pritchard, A. B., McCormick, D. B. & Wright, L. D. (1967) Optical rotatory dispersion studies on the heat denaturation of avidin and the avidin-biotin complex. Biochem. Biophys. Res. Commun. 25: 524-528.
146. Rasmussen, K. M., Barsa, P. M. & McCormick, D. B. (1979) Pyridoxamine (pyridoxine) 5′-phosphate oxidase activity in rat tissues during development of riboflavin or pyridoxine deficiency. Proc. Soc. Exp. Biol. Med. 161: 527-530.
147. Rasmussen, K. M., Barsa, P. M., McCormick, D. B. & Roe, D. A. (1980) Effect of strain, sex and dietary riboflavin on pyridoxamine (pyridoxine) 5′-phosphate oxidase activity in rat tissues. J. Nutr. 110: 1940-1946.
148. Roth, J. A., Chassy, B. M. & McCormick, D. B. (1966) Coenzymatic activities of 2-anilino and 2-morpholino derivatives of FMN with yeast NADPH diaphorase. Biochim. Biophys. Acta 118: 429-431.
149. Roth, J. A. & McCormick, D. B. (1967) Complexing of riboflavin and its 2-substituted analogs with adenosine and other 6-substituted purine derivatives. Photochem. Photobiol. 6: 657-664.
150. 14C-carbonyl-labeled biotin 1-sulfoxide. J. Biol. Chem. 245: 6264-6268.
151. Roughead, Z. K. & McCormick, D. B. (1990a) A qualitative and quantitative assessment of flavins in cows milk. J. Nutr. 120: 382-388.
152. Roughead, Z. K. & McCormick, D. B. (1990b) Flavin composition of human milk. Am. J. Clin. Nutr. 52: 854-857.
153. Roughead, Z. K. & McCormick, D. B. (1991) Urinary riboflavin and its metabolites: Effects of riboflavin supplementation in healthy residents of rural Georgia (USA). Eur. J. Clin. Nutr. 45: 299-307.
154. 14C-norbiotin. J. Biol. Chem. 243: 547-551.
155. Sander, E. G., McCormick, D. B. & Wright, L. D. (1966) Column chromatography of nucleotides over thymidylate-cellulose. J. Chromatogr. 21: 419-423.
156. Sander, E. G., Wright, L. D. & McCormick, D. B. (1965) Evidence for function of metal ion in the activity of dihydroorotase from Zymobacterium oroticum. J. Biol. Chem. 240: 3628-3630.
157. Shiga, K., Tollin, G., Falk, M. C. & McCormick, D. B. (1975) Binding and oxidation-reduction of monoamine oxidase-type 8α-(S-peptidyl)flavins with Azotobacter (Shethna) flavodoxin. Biochem. Biophys. Res. Commun. 66: 227-234.
158. Shih, J.C.H., Rozo, M. L., Wright, L. D. & McCormick, D. B. (1975) Characterization of the growth of Pseudomonas putida LP on lipoate and its analogues: Transport, oxidation, sulphur source, and enzyme induction. J. Gen. Microbiol. 86: 217-227.
159. Shih, J.C.H., Williams, P. B., Wright, L. D. & McCormick, D. B. (1974) Properties of lipoic acid analogs. J. Heterocycl. Chem. 11: 119-123.
160. Shih, J.C.H., Wright, L. D. & McCormick, D. B. (1972) Isolation, identification and characterization of a lipoate-degrading pseudomonad and of a lipoate catabolite. J. Bacteriol. 112: 1043-1051.
161. 2+ with hydrogen phosphate, adenosine 5′-monophosphate, and adenosine 5′-triphosphate. Biochim. Biophys. Acta 148: 655-664.
162. Sigel, H., Griesser, R. & McCormick, D. B. (1969a) On the structure of manganese(II)- and copper(II)-histidine complexes. Arch. Biochem. Biophys. 134: 217-227.
163. Sigel, H., Griesser, R. & McCormick, D. B. (1972) Ternary complexes in solution. XIII. Mixed-ligand complexes of copper(II) or zinc(II) with 2,2′-bipyridyl and thioether carboxylates or some of their sulfoxide or sulfone derivatives. Inorg. Chim. Acta 6: 559-563.
164. 2+ with respect to carboxylic acids and α-oxy- or α-thio-substituted carboxylic acids of biochemical significance. Arch. Biochem. Biophys. 130: 514-520.
165. Sigel, H., MacKenzie, R. E. & McCormick, D. B. (1970) On the structure of copper(II)-histidine complexes. Biochim. Biophys. Acta 200: 411-413.
166. 2+ L-histidine 1:2 complex in solution. J. Am. Chem. Soc. 93: 2041-2044.
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171. 2+ in solution. Arch. Biochem. Biophys. 187: 208-214.
172. Spence, J. T. & McCormick, D. B. (1976) Lipoic acid metabolism in the rat. Arch. Biochem. Biophys. 174: 13-19.
173. Tepper, J. P., McCormick, D. B. & Wright, L. D. (1966) Direct evidence for the conversion of dethiobiotin to biotin in Aspergillus niger. J. Biol. Chem. 241: 5734-5735.
174. 13C-D-glucuronolactone to 5-13C-L-xylulose in a pentosuric human. Biochim. Biophys. Acta 25: 196-198.
175. Tsibris, J.C.M., McCormick, D. B. & Wright, L. D. (1965) Studies on the donor-acceptor complexes relating to the intramolecular association of the riboflavin and adenosine moieties of flavin-adenine dinucleotide. Biochemistry 4: 504-509.
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178. Tu, S. C. & McCormick, D. B. (1969) The biological activity and excretion of 6,7-dimethyl-9-(ω-carboxyalkyl) isoalloxazines in rats. J. Nutr. 97: 307-310.
179. Tu, S. C. & McCormick, D. B. (1972) Insolubilized D-amino acid oxidase: Properties and potential use. Separation Sci. 7: 403-407.
180. Tu, S. C. & McCormick, D. B. (1973) Photoinactivation of porcine D-amino acid oxidase with flavin-adenine dinucleotide. J. Biol. Chem. 248: 6339-6347.
181. Tu, S. C. & McCormick, D. B. (1974) Conformation of porcine D-amino acid oxidase as studied by protein fluorescence and optical rotatory dispersion. Biochemistry 13: 893-899.
182. Uhler, L. D., Crispen, C. R. & McCormick, D. B. (1971) Free amino acid patterns during development of Eurosta solidaginis (Fitch). Comp. Biochem. Physiol. 38: 87-91.
183. Visser, J., McCormick, D. B. & Veeger, C. (1968) Relation between conformation and activities of lipoamide dehydrogenase. II. Some aspects of recombination with FAD analogues. Biochim. Biophys. Acta 159: 257-264.
184. Walker, F. A., Sigel, H. & McCormick, D. B. (1972) Spectral properties of mixed-ligand copper(II) complexes and their corresponding binary parent complexes. Inorg. Chem. 11: 2756-2763.
185. Westendorf, J. & McCormick, D. B. (1980) Isolation of volatile sulfur-containing microbial catabolites of biotin. Internat. J. Vit. Nutr. Res. 50: 62-65.
186. Woods, M. N. & McCormick, D. B. (1964) Effects of dietary phenylalanine on activity of phenylalanine hydroxylase from rat liver. Proc. Soc. Exp. Biol. Med. 116: 427-430.
187. Wu, F.Y.H. & McCormick, D. B. (1971a) The fluorescence quenching of aromatic amino acid and flavin portions of flavinyl peptides. Biochim. Biophys. Acta 229: 440-443.
188. Wu, F.Y.H. & McCormick, D. B. (1971b) Flavin-sensitized photooxidations of tryptophan and tyrosine. Biochim. Biophys. Acta 236: 479-486.
189. Wu, F.Y.H., Tu, S. C., Wu, W. C. & McCormick, D. B. (1970) Characteristics of the fluorescence spectra of apoenzyme and flavin portions of D-amino acid oxidase. Biochem. Biophys. Res. Commun. 41: 381-385.
190. Yamada, Y., Merrill, A. H., Jr. & McCormick, D. B. (1990) Probable reaction mechanisms of flavokinase and FAD synthetase from rat liver. Arch. Biochem. Biophys. 278: 125-130.
191. Yang, C. S., Arsenis, C. & McCormick, D. B. (1964) Microbiological and enzymatic assays of riboflavin analogues. J. Nutr. 84: 167-172.
192. Yang, C. S. & McCormick, D. B. (1967a) Substrate specificity of riboflavin hydrolase from Pseudomonas riboflavina. Biochim. Biophys. Acta 132: 511-513.
193. Yang, C. S. & McCormick, D. B. (1967b) Degradation and excretion of riboflavin in the rat. J. Nutr. 93: 445-453.
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195. Zempleni, J., Galloway, J. R. & McCormick, D. B. (1996b) The identification and kinetics of 7α-hydroxyriboflavin (7-hydroxymethylriboflavin) in blood plasma from humans following oral administration of riboflavin supplements. Int. J. Vit. Nutr. Res. 66: 151-157.
196. Zempleni, J., Galloway, J. R. & McCormick, D. B. (1996c) The metabolism of riboflavin in female patients with liver cirrhosis. Int. J. Vit. Nutr. Res. 66: 237-243.
197. Zempleni, J., McCormick, D. B. & Mock, D. M. (1996d) The identification of biotin sulfone, bisnorbiotin methyl ketone, and tetranorbiotin-1-sulfoxide in human urine. Am. J. Clin. Nutr. 65: 508-511.
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200. Zhang, Z. & McCormick, D. B. (1991) Uptake of N-(4′-pyridoxyl) amines and release of amines by renal cells: A model for transporter-enhanced delivery of bioactive compounds. Proc. Natl. Acad. Sci. (USA) 88: 10407-10410.
201. Zhang, Z. & McCormick, D. B. (1992a) Uptake and metabolism of N-(4′-pyridoxyl)amines by isolated rat liver cells. Arch. Biochem. Biophys. 294: 394-397.
202. Zhang, Z. & McCormick, D. B. (1992b) Uptake and metabolism of 4′(N)-substituted pyridoxamines by cells from the liver and kidneys of rats. In: 1st Internat'l. Congress on Vitamin and Biofactors in Life Science (Kobayashi, T., ed.) pp. 208-211, Center for Academic Publications, Osaka, Japan.
203. Zhang, Z., Smith, E., Surowiec, S. M., Merrill, A. H., Jr. & McCormick, D. B. (1993b) Synthesis of N-(4′-pyridoxyl)-sphingosine and its uptake and metabolism by isolated cells. Membrane Biochem. 10: 53-59.