Flavin Chemistry and Catalysis

144. T.C. Bruice; L. Main; S. Smith and P.Y. Bruice. Preequilibrium Complex Formation and Nucleophilic Addition (and Its Position) As Factors in Flavin-Catalyzed Oxidations. J. Am. Chem. Soc. 1971, 93, 7327.

153. L. Main; G.J. Kasperek and T.C. Bruice. Isoalloxazine(Flavin)Dehydrogenation of Dimethyl trans-1,2-Dihydrophthalate. J. Chem. Soc., Chem. Commun. 1972, 14, 847-8.

155. M. Brüstlein and T.C. Bruice. Demonstration of a Direct Hydrogen Transfer between NADH and a Deazaflavin. J. Am. Chem. Soc. 1972, 94, 6548.

157. L. Main; G.J. Kasperek and T.C. Bruice. Kinetics and Mechanism of the Isoalloxazine (Flavin) Dehydrogenation of Dimethyl Dihydrophthalates. Biochem. 1972, 11, 3991

160. L. Hevesi and T.C. Bruice. 5 vs. 4a-Addition to Isoalloxazine. J. Am. Chem. Soc. 1972, 94, 8277.

163. L. Hevesi and T.C. Bruice. Reaction of Sulfite with Isoalloxazines. Biochem. 1973, 12, 290.

167. T.C. Bruice; L. Hevisi and S. Shinkai. Mechanisms of Formation and Equilibria of 4a and 5 Adducts of an Isoalloxazine. Reaction of 10-(2',6'-Dimethylphenyl)-3-methylisoalloxazine- 6,8-disulfonate with Sulfite in Aqueous Media. Biochem. 1973, 12, 2083.

171. S. Shinkai and T.C. Bruice. The Question of Covalent Intermediate Formation in the Flavine-Catalyzed Carbonyl to Carbinol Oxidation-Reduction Reaction. J. Am. Chem. Soc. 1973, 95, 7526.

173. D.L. Elliot and T.C. Bruice. Evidence for an Intermediate Adduct in the Ethylenediaminetetraacetic Acid Mediated Photoreduction of Flavines. J. Am. Chem. Soc. 1973, 95, 7901.

180. S.B. Smith; M. Brüstlein and T. C. Bruice. Electrophilicity of the 8 Position of the Isoalloxazine (Flavine) Ring System. Comment on the Mechanism of Oxidation of Dihydroisoalloxazine. J. Am. Chem. Soc. 1974, 96, 3696.

185. D. Clerin and T.C. Bruice. A Kinetic Study of the Fate of a Covalent Intermediate of the Type Proposed to be Involved in Flavin Catalysis. J. Am. Chem. Soc. 1974, 96, 5571.

188. S. Shinkai; T. Kunitake and T.C. Bruice. The Importance of 1,2- Enediols in the Reduction of Lumiflavin by a-Ketols. J. Am.Chem. Soc. 1974, 96, 7140.

189. I. Yokoe and T.C. Bruice. Oxidation of Thiophenol and Nitroalkanes by an Electron Deficient Isoalloxazine. J. Am. Chem. Soc. 1975, 97, 450.

191. S.B. Smith and T.C. Bruice. Mechanisms of Isoalloxazine (Flavine) Hydrolysis. J. Am. Chem. Soc. 1975, 97, 2875.

192. R.F. Williams; S. Shinkai and T.C. Bruice. Radical Mechanisms for 1,5-Dihydroflavin Reduction of Carbonyl Compounds. Proc. Natl. Acad. Sci. (USA) 1975, 72, 1763.

195. T.C. Bruice and Y. Yano. Radical Mechanisms for 1,5-Dihydro-5- methylflavine Reduction of Carbonyl Compounds. J. Am. Chem. Soc. 1975, 97, 5263.

202. C. Kemal and T.C. Bruice. Simple synthesis of a 4a-hydroperoxy adduct of a 1,5-dihydroflavin: Preliminary studies of a model for bacterial luciferase. Proc. Natl. Acad. Sci. (USA) 1976, 73, 995.

203. T.C. Bruice. Models and Flavin Catalysis. Progress in Bioorganic Chemistry, Vol. 4; E.T. Kaiser; Ed.; Wiley and Sons, 1976; 1-87.

204. C. Kemal and T.C. Bruice. The Chemistry of an N5-Methyl-1,5- dihydroflavin and Its Aminium Cation Radical. J. Am. Chem. Soc. 1976, 98, 3955.

207. T.C. Bruice. Some Physical Organic Studies Dealing with Flavin Catalysis. Flavins Flavoproteins, Proc. Int. Symp., 5th 1976, Meeting Date 1975, 244-260.

209. R.F. Williams and T.C. Bruice. The Kinetics and Mechanisms of 1,5-Dihydroflavin Reduction of Carbonyl Compounds and Flavin Oxidation of Alcohols. 2. Ethyl Pyruvate, Pyruvamide and Pyruvic Acid. J. Am. Chem. Soc. 1976, 98, 7752.

210. T.C. Bruice and J.P. Taulane. The Kinetics and Mechanisms of 1,5-Dihydroflavin Reduction of Carbonyl Compounds and Flavin Oxidation of Alcohols. 3. Oxidation of Benzoin by Flavin and Reduction of Benzil by 1,5-Dihydroflavin. J. Am. Chem. Soc. 1976, 98, 7769.

211. R.F. Williams; S.S. Shinkai and T.C. Bruice. Kinetics and Mechanisms of the 1,5-Dihydroflavin Reduction of Carbonyl Compounds and the Flavin Oxidation of Alcohols. 4. Interconversion of Formaldehyde and Methanol. J. Am. Chem. Soc. 1977, 99, 921.

212. C. Kemal; T.W. Chan and T.C. Bruice. Chemiluminescent reactions and electrophilic oxygen donating ability of 4a- hydroperoxyflavins: General synthetic method for the preparation of N5-alkyl-1,5-dihydroflavins. Proc. Natl. Acad. Sci. (USA) 1977, 74, 405.

213. T.W. Chan and T.C. Bruice. One and Two Electron Transfer Reactions of Glucose Oxidase. J. Am. Chem. Soc. 1977, 99, 2387.

219. T.C. Bruice; T.W. Chan; J.P. Taulane; I. Yokoe; D.L. Elliott; R.F. Williams and M. Novak. Changes in the Chemistry of an Isoalloxazine Brought About by Substitution at the 7 and 8 Positions by a Strongly Electronegative Substituent. J. Am. Chem. Soc. 1977, 99, 6713.

220. R.L. Chan and T.C. Bruice. The Chemistry of an Electron- Deficient 5-Deazaflavin. 8-Cyano-10-methyl-5- deazaisoalloxazine. J. Am. Chem. Soc. 1977, 99, 6721.

221. C. Kemal and T.C. Bruice. Chemiluminescence Accompanying the Decomposition of 4a-Flavin Alkyl Peroxide. Model Studies of Bacterial Luciferase. J. Am. Chem. Soc. 1977, 99, 7064.

222. C. Kemal; T.W. Chan and T.C. Bruice. Reactions of 3O2 with Dihydroflavins. 1. N3,5-Dimethyl-1,5-Dihydrolumiflavin and 1,5-Dihydroisoalloxazines. J. Am. Chem. Soc. 1977, 99, 7272.

223. T.W. Chan and T.C. Bruice. Reaction of Nitroxides with 1,5-Dihydroflavins and N3,5-Dimethyl-1,5-Dihydrolumiflavin. J. Am. Chem. Soc. 1977, 99, 7287.

224. M. Novak and T.C. Bruice. Oxidation of 9-Hydroxy- and 9- Methoxyfluorene Carbanions by Flavin. Proof of Radical Mechanism. J. Am. Chem. Soc. 1977, 99, 8079.

231. T.W. Chan and T.C. Bruice. Importance of C4a- and N5-Covalent Adducts in the Flavin Oxidation of Carbanions. Biochem. 1978, 17, 4784.

232. R.L. Chan and T.C. Bruice. Characterization and One- and Two- Electron Redox Chemistry of 1,5-Dicarba-1,5- dideazaisoalloxazines (Flavins). J. Am. Chem. Soc. 1978, 100, 7375.

234. G. Tollin; R.L. Chan; T.R. Malefyt and T.C. Bruice. Some One Electron Reduction Products of Flavin Analogs: Cyanoisoalloxazines and Deazaisoalloxazines. Photochem. Photobiol. 1979, 29, 233-43.

235. C. Kemal and T.C. Bruice. Transfer of O2 from a 4a- Hydroperoxyflavin Anion to a Phenolate Ion. A Flavin- Catalyzed Dioxygenation Reaction. J. Am. Chem. Soc. 1979, 101, 1635.

236. S. Ball and T.C. Bruice. 4a-Hydroperoxyflavin N-Oxidation of Tertiary Amines. J. Am. Chem. Soc. 1979, 101, 4017.

241. A. Miller and T.C. Bruice. Oxidations by a 4a- Hydroperoxyisoalloxazine hindered in the 9a and 10a Positions. J. Chem. Soc., Chem. Comm. 1979, 20, 896-7.

242. M. Novak; A. Miller; T.C. Bruice and G. Tollin. The Mechanism of Flavin 4a Substitution Which Accompanies Photolytic Decarboxylation of a-substituted Acetic Acids. J. Am. Chem. Soc. 1980, 102, 1465.

243. M. Novak and T.C. Bruice. Mechanistic Investigation of the Oxidation of the Carbanion of Methyl 2-Methoxy-2- phenylacetate by an Isoalloxazine. J. Chem. Soc., Chem. Commun. 1980, 9, 372-4.

244. T.C. Bruice and A. Miller. Products of the Decomposition of the Anion of a 4a-Hydroperoxyisoalloxazine Hindered in the 9a and 10a Positions. J. Chem. Soc., Chem. Commun. 1980, 15, 693-4.

245. S. Muto and T.C. Bruice. Dioxygen Transfer from 4a- Hydroperoxyflavin Anion. 2. Oxygen Transfer to the 10 Position of 9-Hydroxyphenanthrene Anions and to 3,5-Di-tert- butylcatechol Anion. J. Am. Chem. Soc. 1980, 102, 4472.

246. M. Iwata; T.C. Bruice; H.L. Carrell and J.P. Glusker. Reactions of 4a-Peroxides and 4a-Pseudobases of N10- and N5- Phenethylflavins. J. Am. Chem. Soc. 1980, 102, 5036.

247. T.C. Bruice. Mechanisms of Flavin Catalysis. Accts. Chem. Res. 1980, 13, 256-262.

248. S. Ball and T.C. Bruice. Oxidation of Amines by a 4a- Hydroperoxyflavin. J. Am. Chem. Soc. 1980, 102, 6498.

250. Bruice, Thomas C.. Carbon acid oxidations and oxygen activation by flavins. Advances in Chemistry Series 1980, 191(Biomimetic Chem.), 89-118.

251. S. Muto and T.C. Bruice. Dioxygen Transfer from 4a- Hydroperoxyflavin Anion. 3. Oxygen Transfer to the 3-Position of Substituted Indoles. J. Am. Chem. Soc. 1980, 102, 7559.

252. P.T. Shepherd and T.C. Bruice. Formation of a Non- chemiluminescent Excited-State Species in the Decomposition of 4a-(Alkylperoxy)flavins. J. Am. Chem. Soc. 1980, 102, 7774.

253. E.J. Nanni; D.T. Sawyer; S.S. Ball and T.C. Bruice. Redox Chemistry of N5-Ethyl-4a-hydroperoxy-3-methyllumiflavin in Dimethylformamide. Evidence for the Formation of the N5- Ethyl-4a-hydroperoxy-3-methyllumiflavin Anion via Radical- Radical Coupling with Superoxide Ion. J. Am Chem. Soc. 1981, 103, 2797.

254. S. Ball and T.C. Bruice. The Chemistry of 1-Carba-1-deaza-N5- ethyl-N3-methyllumiflavins. Influence of the N1 upon the Reactivity of Flavin 4a-Hydroperoxides. J. Am. Chem. Soc. 1981, 103, 5494.

258. A. Wessiak and T.C. Bruice. On the Nature of the Intermediate between 4a-Hydroperoxyflavin and 4a-Hydroxyflavin in the Hydroxylation Reaction of p-Hydroxybenzoate Hydroxylase. Synthesis of 6-Aminopyrimidine-2,4,5(3H)-triones and the Mechanism of Aromatic Hydroxylation by Flavin Monooxygenases. J. Am. Chem. Soc. 1981, 103, 6996.

259. Shepherd, Peter T.; Bruice, Thomas C.. Chemiluminescence derived from 4a-(alkylperoxy) flavins. Biolumin. Chemilumin., [Int. Symp. Anal. Appl. Biolumin. Chemilumin.], 2nd 1981, Meeting Date 1980, 391-4.

260. Bruice, Thomas C.. A progress report on studies of the activation of molecular oxygen by dihydroflavins. Developments in Biochemistry 1982, 21(Flavins Flavoproteins), 265-77.

261. G. Eberlein and T.C. Bruice. One- and Two-Electron Reduction of Oxygen by 1,5-Dehydroflavins. J. Am. Chem. Soc. 1982, 104, 1449.

263. S. Muto and T.C. Bruice. Dioxygen Transfer from 4a- Hydroperoxyflavin Anion. 4. Dioxygen Transfer to Phenolate Anion as a Means of Aromatic Hydroxylation. J. Am. Chem. Soc. 1982, 104, 2284.

266. E.B. Skibo and T.C. Bruice. Preparation and Study of a Low- Potential Flavin Analogue. J. Am. Chem. Soc. 1982, 104, 4982.

268. Bruice, Thomas C.. 4a-Peroxyflavins. Oxidases Relat. Redox Syst., Proc. Int. Symp., 3rd 1982, Meeting Date 1979, 423-46.

272. T.C. Bruice. Leaving Group Tendencies and the Rates of Monooxygen Donation by Hydrogen Peroxide, Organic Hydroperoxides, and the Peroxycarboxylic Acids. J. Am. Chem. Soc., Chem. Commun. 1983, 1, 14-15.

273. T.C. Bruice; J.B. Noar; S.S. Ball and U.V. Venkataram. Mono-oxygen Donation Potential of 4a-Hydroperoxyflavins as Compared with Those of a Percarboxylic Acid and other Hydroperoxides. Monooxygen Donation to Olefin, Tertiary Amine, Alkyl Sulfide, and Iodide Ion. J. Am. Chem. Soc. 1983, 105, 2452.

274. E.B. Skibo and T.C. Bruice. High- and Low-Potential Flavin Mimics (Based on the Pyrimidino[5,4-g]pteridine and Imidazo[4,5-g]pteridine System). 1. General Chemistry. J. Am. Chem. Soc. 1983, 105, 3304.

275. E.B. Skibo and T.C. Bruice. High- and Low-Potential Flavin Mimics. 2. 3,7,10-Trimethyl-(1H,3H,5H,7H,9H,10H)- pyrimido[5,4,-g]-pteridine-2,4,6,8-tetrone Dianion Reduction of Carbonyl, Nicotinamides, and Alkyl Disulfide Functional Groups. J. Am. Chem. Soc. 1983, 105, 3316.

277. A. Wessiak and T.C. Bruice. Synthesis and Study of a 6-Amino- 5-oxo-3H,5H-uracil and Derivatives. The Structure of an Intermediate Proposed in Mechanisms of Flavin and Pterin Oxygenases. J. Am. Chem. Soc. 1983, 105, 4809.

280. G. Eberlein and T.C. Bruice. The Chemistry of a 1,5-Diblocked Flavin. 1. Interconversion of the Reduced, Radical and Oxidized Forms of 1,10-Ethano-5-ethyllumiflavin. J. Am. Chem. Soc. 1983, 105, 6679.

281. G. Eberlein and T.C. Bruice. The Chemistry of a 1,5-Diblocked Flavin. 2. Proton and Electron Transfer Steps in the Reaction of Dihydroflavins with Oxygen. J. Am. Chem. Soc. 1983, 105, 6685.

284. A. Wessiak; J.B. Noar and T.C. Bruice. The possibility that the spectrum of intermediate two, seen in the course of reaction of flavoenzyme phenol hydroxylases, may be attributable to iminol isomers of a flavin-derived 6-arylamino-5- oxo(3H,5H)uracil. Proc. Natl. Acad. Sci. (USA) 1984, 81, 332.

285. L.-C. Yuan and T.C. Bruice. Redox Reactions of a Tetrahydro- /Hexahydropyrido[2,3-d3:6,5-d']dipyrimidine Tetrone Couple. A High vs. Low Potential 5-Carba-5-deazaflavin Mimic. J. Am. Chem. Soc. 1984, 106, 1530.

287. O.L. Farng and T.C. Bruice. Carbon-Carbon Double Bond Formation Accompanying Hydride Transfer from a Carbanion to a 5-Carbalumiflavin. J. Chem. Soc., Chem. Commun. 1984, 3, 185-6.

288. T.C. Bruice. Oxygen-Flavin Chemistry. Isr. J. Chem. 1984, 24, 54.

291. A. Wessiak; L.M. Schopfer; L.C. Yuan; T.C. Bruice; and V. Massey. Use of riboflavin-binding protein to investigate steric and electronic relationships in flavin analogs and models. Proc. Natl. Acad. Sci. 1984, 81, 4246.

292. U.V. Venkataram and T.C. Bruice. Determination of the Kinetic pKa of a Flavin 4a-Pseudobase from a Study of the Hydrolysis of 4a-Hydroxy-5-ethyl-3-methyl-lumiflavin in H2O. The Oxygen Donation Potential of 4a-Hydroperoxyflavins. J. Chem. Soc., Chem. Commun. 1984, 14, 899-900.

293. U.V. Venkataram and T.C. Bruice. On the Mechanism of Flavin- Catalyzed Dehydrogenation a, ß to an Acyl Function. The Mechanism of 1,5-Dihydroflavin Reduction of Malemides. J. Am. Chem. Soc. 1984, 106, 5703.

296. G. Eberlein; T.C. Bruice; R.A. Lazarus; R. Henrie and S.J. Benkovic. The Interconversion of the 5,6,7,8-Tetrahydro-, 7,8-Dihydro-, and Radical Forms of 6,6,7,7-Tetramethyldihydropterin. A Model for the Biopterin Center of Aromatic Amino Acid Mixed Function Oxidases. J. Am. Chem. Soc. 1984, 106, 7916.

297. Bruice, Thomas C.. Flavin oxygen chemistry brought to date. Flavins Flavoproteins, Proc. Int. Symp., 8th 1984, 45-55.

317. E.B. Skibo and T.C. Bruice. High- and Low-Potential Flavin Mimics. 3. 3,7,10-Trimethyl-(1H,3H,5H,7H,9H,10H)- pyrimido[5,4-g]pteridine-2,4,6,8-tetrone-Mediated Reduction of Carbon-Carbon Double Bonds a-ß to an Acyl Function. J. Am. Chem. Soc. 1986, 108, 1650.

363. S.-R. Keum; D.H. Gregory; and T.C. Bruice. Oxidation of Aminophenols by 4a-Hydroperoxy-5-ethyllumiflavin Anion. Flavoenzyme Hydroxylase Mechanism. J. Am. Chem. Soc. 1990, 112, 2711.

366. T.W. Kaaret and T.C. Bruice. Electrochemical Luminescence with N(5)-Ethyl-4a-Hydroxy-4a,5-Dihydrolumiflavin. The Mechanism of Bacterial Luciferase. Photochem. Photobiol. 1990, 51, 629.

464. Y-J. Zheng & T. C. Bruice. Identifying the Intermediate in the Dioxygen Transfer from 4a-Hydroperoxyflavin Anion to Phenolate and Indole Anions. Bioorganic Chem. 1998, 25, 331.