Bruce Branchaud
Education
B.S., University of Massachusetts, Dartmouth, 1976. Ph.D., Harvard University, 1981 (R. B. Woodward). Postdoctoral: Massachusetts Institute of Technology, 1981-83 (Christopher T. Walsh). Honors and Awards: National Institutes of Health Postdoctoral Fellowship, 1981-83; Alfred P. Sloan Fellow, 1987-89; Visiting Professor, Phillips Universität, Marburg, Germany, 1991; Visiting Professor, Harvard University, 1992, 1993. Fellow of the American Association for the Advancement of Science, 2010-present. At Oregon since 1983.
Bruce Branchaud has been a faculty member in the Department of Chemistry at the University of Oregon from 1983 to the present. He is currently Professor Emeritus. He is teaching, working on collaborative research with other faculty and co-leading the Master’s Industrial Internship Program in Organic Synthesis & Process Development.
He is an organic chemist, a bioorganic chemist and a chemical biologist. His scientific contributions over the past 3 decades have been in several areas including organic chemistry, biological chemistry, chemical biology, organometallic chemistry and nanochemistry.
Selected accomplishments include (1) several natural products total syntheses, (2) the development of coenzyme B12 model compounds for new methods in organic synthesis, (3) the study of the mechanisms of several enzymes, especially the copper-tyrosine radical enzyme galactose oxidase, (4) synthetic molecular machines, specifically synthetic organic molecular motors with directed bond rotation in a single direction, and (5) the chemistry and biology of nitrated lipids, products of oxidative metabolism of lipid unsaturated fatty acids.
In addition to his academic career, he held several leadership positions in the biotech industry from 2005 to 2011. He worked for Invitrogen then for Life Technologies. Life Technologies was formed by the merger of Invitrogen and Applied Biosystems at the end of 2008.
He was Director of Global Chemistry for Invitrogen, including leading the Molecular Probes chemistry R&D organization, 2005-2008. He then worked in Global R&D in Life Technologies, reporting directly to the Chief Scientific Officer, 2008-2011. He was a Research Fellow, Leader for Emerging Technologies–Chemistry and Chair of the Life Technologies Science Council from 2008 to 2010. He was a Research Fellow, Leader for Emerging Technologies–Chemistry, member of the Life Technologies Science Council and co-leader of S&T Intelligence in 2011.
Publications
"ATP Analogs with Non-transferable Groups in the g Position As Inhibitors of Glycerol Kinase", Bystrom, C. E.; Pettigrew, D. W.; Remington, S. J.; Branchaud, B. P. Bioorganic & Medicinal Chemistry Letters 1997, 7, 2613-2616.
Branchaud, B. P.; Meier, M. S.; Malekzadeh, M. N. “New Synthetic Methods via Free Radicals. Free Radical Generation via Photolytic Homolysis of Alkylcobaloxime Carbon-Cobalt Bonds. Efficient Radical Trapping with Useful Functional Groups” Journal of Organic Chemistry 1987, 52, 212-17.
Branchaud, B. P.; Yu, G. X. “Cobaloxime-Mediated Radical Alkyl-Nitroalkyl Anion Cross Coupling” Tetrahedron Letters 1988, 29, 6545-8.
Branchaud, B. P.; Choi, Y. L. “Effect of a Remote Ligand Substituent on Premature beta-Hydrogen Elimination in a Cobaloxime-Mediated Radical Alkyl-Alkenyl Cross Coupling” Tetrahedron Letters 1988, 29, 6037-8.
Branchaud, B. P.; Meier, M. S. “Synthesis of Ammonium 3-Deoxy-D-manno-2-octulosonate (Ammonium KDO) from D-Mannose via Cobaloxime-Mediated Radical Alkyl-Alkenyl Cross Coupling” Tetrahedron Letters 1988, 29, 3191-4.
Branchaud, B. P.; Meier, M. S.; Choi, Y. “Alkyl-Alkenyl Cross Coupling via Alkyl Cobaloxime Radical Chemistry. An Alkyl Equivalent to the Heck Reaction Compatible with Common Organic Functional Groups” Tetrahedron Letters 1988, 29, 167-70.
Branchaud, B. P.; Choi, Y. L. “Cobaloxime-Mediated Radical Alkyl-Heteroaromatic Substitution” Journal of Organic Chemistry 1988, 53, 4638-41.
Branchaud, B. P.; Meier, M. S. “A Novel Strategy for the Synthesis of Ammonium 3-Deoxy-D-Manno-2-Octulosonate (Ammonium KDO) From Lower Monosaccharides. C-C Bond Construction on C6 of D-mannose via Cobaloxime-Mediated Radical Alkyl-Alkenyl Cross Coupling” Journal of Organic Chemistry 1989, 54, 1320-6.
Karpusas, M.; Branchaud, B.; Remington, S. J. “Proposed Mechanism for the Condensation Reaction of Citrate Synthase: 1.9-A Structure of the Ternary Complex with Oxaloacetate and Carboxymethyl Coenzyme A” Biochemistry 1990, 29, 2213-9. Ahrens, M.; Macheroux, P.; Eberhard, A.; Ghisla, S.; Branchaud, B. P.; Hastings, J. W. “Boronic Acids as Mechanistic Probes for the Bacterial Luciferase Reaction” Photochemistry and Photobiology 1991, 54, 295-9.
Branchaud, B. P.; Detlefsen, W. D. “Cobaloxime-Catalyzed Radical Alkyl-Styryl Cross Couplings” Tetrahedron Letters 1991, 32, 6273-6.
Branchaud, B. P.; Yu, G. X. “Some Carbon-Carbon Bond Constructions on Monosaccharides Using Cobaloxime-Mediated Radical Alkyl-Nitroalkylanion Cross Coupling Reactions” Tetrahedron Letters 1991, 32, 3639-42.
Branchaud, B. P.; Yu, G. X. “Stereoelectronic Control of Electron Transfer in the Oxidative Addition of [py(dmgH)2CoI]-Na+ to Carbohydrate Secondary Iodides” Organometallics 1991, 10, 3795-7. Branchaud, B. P.; Glenn, A. G.; Stiasny, H. C. “Round-Trip Radical Probes: Ring Cleavage of the Bicyclo[1.1.1]Pentylcarbinyl Radical” Journal of Organic Chemistry 1991, 56, 6656-9. Montague-Smith, M. P.; Wachter, R. M.; Branchaud, B. P. “Preparation of Fully Oxidized Active and Reduced Inactive Forms of Galactose Oxidase from Dactylium dendroides using Ferricyanide-Containing Oxidizing and Ferrocyanide-Containing Reducing Forms of Ion Exchange Resins” Analytical Biochemistry 1992, 207, 353-5.
Branchaud, B. P.; Slade, R. M.; Janisse, S. K. “A Cobaloxime-Mediated Radical Route to Butenolides” Tetrahedron Letters 1993, 34, 7885-8.
Branchaud, B. P.; Yu, G. X. “An Example of the Persistent Radical Effect in Cobaloxime-Mediated Radical Alkyl-Alkenyl Cross Coupling” Organometallics 1993, 12, 4262-4.
Branchaud, B. P.; Montague-Smith, M. P.; Kosman, D. J.; McLaren, F. R. “Mechanism-Based Inactivation of Galactose Oxidase: Evidence for a Radical Mechanism” Journal of the American Chemical Society 1993, 115, 798-800.
Branchaud, B. P.; Slade, R. M. “A Cobaloxime-Mediated Synthesis of the Ras Farnesyl-Protein Transferase Inhibitor Chaetomellic Acid A” Tetrahedron Letters 1994, 35, 4071-2.
Bullock, T. L.; Branchaud, B.; Remington, S. J. “Structure of the Complex of L-Benzylsuccinate with Wheat Serine Carboxypeptidase II at 2.0-A Resolution” Biochemistry 1994, 33, 11127-34.
Friestad, G. K.; Branchaud, B. B. “Intramolecular Pd-Catalyzed Aryl-Enone Conjugate Additions. Control of Reductive vs Non-Reductive Cyclization” Tetrahedron Letters 1995, 36, 7047-50.
Detlefsen, W. D.; Branchaud, B. P. “Attachment of a Styryl Group to the 6-Position of a Protected Penicillanic Acid via Cobaloxime-Mediated Radical Alkyl-Alkenyl Cross Coupling” Bioorganic & Medicinal Chemistry Letters 1996, 6, 2289-2292.
Gage, J. L.; Branchaud, B. P. “Exploratory Studies on Reactions of Cobaloxime pi-Cations with C-Nucleophiles: Irreversible Alkene Decomplexation versus Nucleophilic Capture” Journal of Organic Chemistry 1996, 61, 831-7.
Slade, R. M.; Branchaud, B. P. “Oxidative Addition of py(dmgH)2Co-Na+ to a Ribofuranosyl Bromide: An Unusual Reaction with the Cobaloxime Ligand” Organometallics 1996, 15, 2585-2587.
Wachter, R. M.; Branchaud, B. P. “Thiols as Mechanistic Probes for Catalysis by the Free Radical Enzyme Galactose Oxidase” Biochemistry 1996, 35, 14425-14435.
Wachter, R. M.; Branchaud, B. P. “Molecular Modeling Studies on Oxidation of Hexopyranoses by Galactose Oxidase. An Active Site Topology Apparently Designed To Catalyze Radical Reactions, Either Concerted or Stepwise” Journal of the American Chemical Society 1996, 118, 2782-9.
Bystrom, C. E.; Pettigrew, D. W.; Remington, S. J.; Branchaud, B. P. “ATP Analogs with Non-Transferable Groups in the gamma Position as Inhibitors of Glycerol Kinase” Bioorganic & Medicinal Chemistry Letters 1997, 7, 2613-2616.
Friestad, G. K.; Branchaud, B. P. “A New Approach to the Pancratistatin C-ring from D-Glucose: Ferrier Rearrangement, Pseudoinversion and Pd-Catalyzed Cyclizations” Tetrahedron Letters 1997, 38, 5933-5936.
Gage, J. L.; Branchaud, B. P. “A Synthesis of (-)-Tashiromine and Formal Synthesis of (+)-Tashiromine Utilizing a Highly Enantioselective Pyrrole/Cobaloxime pi-Cation Cyclization” Tetrahedron Letters 1997, 38, 7007-7010.
Grubb, L. M.; Branchaud, B. P. “Complete Retention of Configuration in a Cobaloxime pi-Cation-Mediated Cyclization of an (omega-Hydroxy-beta-hydroxyalkyl)cobaloxime” Journal of Organic Chemistry 1997, 62, 242-243.
Wachter, R. M.; Montague-Smith, M. P.; Branchaud, B. P. “beta-Haloethanol Substrates as Probes for Radical Mechanisms for Galactose Oxidase” Journal of the American Chemical Society 1997, 119, 7743-7749.
Gage, J. L.; Weakley, T. J. R.; Branchaud, B. P. “Bis[2,3-Butanedione dioximato(1-)-N,N'](pyridine){[(R)-5,6,7,8-tetrahydro-8-indolizinyl]methyl}cobalt(III)” Acta Crystallographica, Section C: Crystal Structure Communications 1998, C54, 22-24.
Grubb, L. M.; Brown, K. A.; Branchaud, B. P. “Tetrahydrofuran, tetrahydropyran and oxepane formation by cobaloxime pi-cation cyclizations” Tetrahedron Letters 1998, 39, 3447-3448.
Slade, R. M.; Branchaud, B. P. “Cross Coupling of Alkyl Cobaloximes with Maleic Anhydrides. Basic Studies and Applications to the Synthesis of Chaetomellic Acid A Anhydride and C-Glycosyl Maleic Anhydrides” Journal of Organic Chemistry 1998, 63, 3544-3549.
Wachter, R. M.; Branchaud, B. P. “Construction and Analysis of a Semi-Quantitative Energy Profile for the Reaction Catalyzed by the Radical Enzyme Galactose Oxidase” Biochimica et Biophysica Acta 1998, 1384, 43-54.
Branchaud, B. P. “Free Radicals as a Result of Dioxygen Metabolism” Metal Ions in Biological Systems 1999, 36, 79-102.
Bystrom, C. E.; Pettigrew, D. W.; Branchaud, B. P.; O'Brien, P.; Remington, S. J. “Crystal Structures of Escherichia coli Glycerol Kinase Variant S58->W in Complex with Nonhydrolyzable ATP Analogs Reveal a Putative Active Conformation of the Enzyme as a Result of Domain Motion” Biochemistry 1999, 38, 3508-3518.
Grubb, L. M.; Dowdy, A. L.; Blanchette, H. S.; Friestad, G. K.; Branchaud, B. P. “An Approach to (+)-Pancratistatin from D-glucose: a Conformational Lock Solves a Stereochemical Problem” Tetrahedron Letters 1999, 40, 2691-2694.
Isobe, H.; Branchaud, B. P. “Epoxide Deoxygenation Mediated by Salen Complexes” Tetrahedron Letters 1999, 40, 8747-8749.
Nishikubo, Y.; Branchaud, B. P. “Cobaloxime pi-Cation Steric and Stereoelectronic Effects: The Amazing Effect of a Single Methyl Group Adjacent to the Site of Reaction” Journal of the American Chemical Society 1999, 121, 10924-10927.
Turner, B. E.; Branchaud, B. P. “Probing the Radical Mechanism of Galactose Oxidase Using an Ultrafast Radical Probe” Bioorganic & Medicinal Chemistry Letters 1999, 9, 3341-3346.
Yu, G.-X.; Tyler, D. R.; Branchaud, B. P. “Thermal and Photochemical Epimerization/Equilibration of Carbohydrate Cobaloximes” Journal of Organic Chemistry 2001, 66, 5687-5691.
Branchaud, B. P.; Turner, B. E. “Galactose Oxidase: Probing Radical Mechanism with Ultrafast Radical Probe” Methods in Enzymology 2002, 354, (Enzyme Kinetics and Mechanism, Part F), 415-425.
Branchaud, B. P.; Blanchette, H. S. “Highly Stereoselective Friedel-Crafts Alkylations of Unactivated Benzenes by Episulfonium Ion Cyclizations” Tetrahedron Letters 2002, 43, 351-353.
Dahl, B. J.; Branchaud, B. P. “Synthesis and Characterization of a Functionalized Chiral Biaryl Capable of Exhibiting Unidirectional Bond Rotation” Tetrahedron Letters 2004, 45, 9599-9602.
Remington, S. J.; Wachter, R. M.; Yarbrough, D. K.; Branchaud, B.; Anderson, D. C.; Kallio, K.; Lukyanov, K. A. “zFP538, a Yellow-Fluorescent Protein from Zoanthus, Contains a Novel Three-Ring Chromophore” Biochemistry 2005, 44, 202-212.
Schopfer, F. J.; Baker, P.R. S.; Giles, G.; Chumley, P.; Batthyany, C.; Crawford, J.; Patel, R. P.; , Hogg, N.; Branchaud, B. P.; Lancaster, J. R. Jr; Freeman, B. A. “Fatty Acid Transduction of Nitric Oxide Signaling. Nitrolinoleic Acid Is A Hydrophobically Stabilized Nitric Oxide Donor,” Journal of Biological Chemistry 2005, 280, 19289–19297.
Robak, A. J.; Branchaud, B. P., First example of a molecularly imprinted polymer incorporating a difunctionalized alloxazine flavin isomer. Tetrahedron Letters 2005, 46, 5651-5654.
Baker, P. R. S.; Lin, Y.; Schopfer, F. J.; Woodcock, S. R.; Groeger, A. L.; Batthyany, C.; Sweeney, S.; Long, M. H.; Iles, K. E.; Baker, L. M. S.; Branchaud, B. P.; Chen, Y. E.; Freeman, B. A., Fatty Acid Transduction of Nitric Oxide Signaling: Multiple nitrated unsaturated fatty acid derivatives exist in human blood and urine and serve as endogenous peroxisome proliferator activated receptor ligands. Journal of Biological Chemistry 2005, 280, 42464-42475.
Woodcock, S. R.; Branchaud, B. P., Effect of ether versus ester tethering on Heck cyclizations. Tetrahedron Letters 2005, 46, 7213-7215.
Lin, Y.; Dahl, B. J.; Branchaud, B. P., Net directed 180 Deg aryl-aryl bond rotation in a prototypical achiral biaryl lactone synthetic molecular motor. Tetrahedron Letters 2005, 46, 8359-8362.
Trumbull, K. A.; Branchaud, B. P., An oxidatively releasable caging group that senses lipid peroxidation. Bioorganic & Medicinal Chemistry Letters 2005, 15, 5544-5547.
Batthyany, C.; Schopfer, F. J.; Baker, P. R. S.; Duran, R.; Baker, L. M. S.; Huang, Y.; Cervenansky, C.; Branchaud, B. P.; Freeman, B. A. Reversible Post-translational Modification of Proteins by Nitrated Fatty Acids in Vivo, Journal of Biological Chemistry 2006, 281, 20450-20463.
Woodcock, S. R.; Marwitz, A. J. V.; Bruno, P.; Branchaud, B. P. Synthesis of Nitrolipids. All Four Possible Diastereomers of Nitrooleic Acids: ( E)- and ( Z)-, 9- and 10-Nitro-octadec-9-enoic Acids, Organic Letters 2006, 8,.3931-3934.
Dahl, B. J.; Branchaud, B. P. 180° Unidirectional Bond Rotation in a Biaryl Lactone Artificial Molecular Motor Prototype, Organic Letters 2006, 8, 5841-5844.
Baker, L. M. S.; Baker, P. R. S.; Golin-Bisello, F.; Schopfer, F. J.; Fink, M.; Woodcock, S. R.; Branchaud, B. P.; Radi, R.; Freeman, B. A. “Nitro-Fatty Acid Reaction With Glutathione and Cysteine: Kinetic Analysis of Thiol Alkylation by a Michael Addition Reaction” Journal of Biological Chemistry 2007, 282, 31085–31093.
Ying, L.-Q.; Branchaud, B. P., Purification of Tetracysteine-Tagged Proteins by Affinity Chromatography Using a Non-Fluorescent, Photochemically Stable Bisarsenical Affinity Ligand. Bioconjugate Chemistry 2011, 22, 987-992.
Ying, L.-Q.; Branchaud, B. P., Selective labeling and monitoring pH changes of lysosomes in living cells with fluorogenic pH sensors. Bioorganic & Medicinal Chemistry Letters 2011, 21, 3546–3549.
Ying, L.-Q.; Branchaud, B. P., Design of a reversible biotin analog and applications in protein labeling, detection, and isolation. Chemical Communications 2011, 47, 8593-8595.