Student and Faculty Publications

PDF iconChemistry & Biochemistry Senior Thesis Titles

* designated student author

Bryan S. Holtzman,*Eric T. Roberts,*Nicholas S. Caminiti,*Jacob A. Fox,*Madison B. Goodstein,*Staci A. Hill,*Zitong B. Jia, * Isabelle N.-M. Leibler,*Michael L. Martini,*Gina M. Mendolia,Molly S. Costanza-Robinson, and Richard C. Bunt, Ligand and base additive effects on the reversibility of nucleophilic addition in palladium-catalyzed allylic aminations monitored by nucleophile crossover. Tetrahedron Lett. 2017, 58, 432.

Pedroso, M. M.; Selleck, C.; Enculescu, C.; Harmer, J.; Mitić, N.; Craig, W. A.; *Helweh, W.; Hugenholtz, P.; Tyson, G. W; David L. Tierney, D. L.; Larrabee, J. A.; Schenk, G. “An uncultured microbiome from a frozen environment harbours a highly efficient antibiotic-degrading metallo-β-lactamase” Metallomics 2017,  submitted.

Selleck, C.; Larrabee, J. A.; Harmer, J.; Guddat, L. W.; Mitic, N.; *Helweh, W.; Ollis, D. L.; Craig, W. R.; Tierney, D. L.; Pedroso, M. M.; Schenk, G. “AIM-1: An antibiotic-degrading metallohydrolase that displays mechanistic flexibility” Chem. Eur. J. 2016, 22, 17704-17714, DOI: 10.1002/chem.201602762.

*Kipouros, I.; *Fica-Contreras, S. M.; *Bowe, G. J. K.;·Choi, S. "Oxidation of 5'-dGMP, 5'-dGDP, and 5'-dGTP by a Platinum(IV) Complex" J. Biol. Inorg. Chem. 2015, 20, 1327-1341. DOI: 10.1007/s00775-015-1312-0

Starus, A.; Nocek, B.; Bennett, B.; Larrabee, J. A.; *Shaw, D. L.; *Sae-Lee, W.; *Russo, M. T.; Gillner, D. M.; Makowska-Grzyska, M.; Joachimiak, A.; Holz, R. C. “Inhibition of the dapE-encoded N-succinyl-L,L-diaminopimelic acid desuccinylase from Neisseria meningitides by L-captopril” Biochem. 2015, 54, 4834-4844, DOI: 10.1021/acs.biochem.5b00475.

*Nicholas S. Caminiti,*Madison B. Goodstein, *Isabelle N.-M . Leibler,*Bryan S. Holtzman, *Zitong B. Jia,  *Michael L. Martini, *Nathaniel C. Nelson,and Richard C. Bunt, Reversible nucleophilic addition can lower the observed enantioselectivity in palladium-catalyzed allylic amination reactions with a variety of chiral ligands. Tetrahedron Lett. 2015, 56, 5445.

Bernhardt HS, Sandwick RK. “Purine biosynthetic intermediate-containing ribose-phosphate polymers as evolutionary precursors to RNA.” J Mol Evol. 2014, 79, 91-104. doi: 10.1007/s00239-014-9640-1.

Prozument, K.; Park, B.G.; Shaver. R.G.; Vasiliou, A.K.; Oldham, J.M.; David, D.E.; Muenter, J.S.; Stanton, J.F.; Suits, A.G.; Ellison, G.B.; Field, R.W. Chirped-pulse millimeterwave spectroscopy for dynamics and kinetics studies for pyrolysis reactions, Physical Chemistry Chemical. Physics, 2014, 16, 15739. (Selected as Cover Article)

Charlotte Majerczyk, Mitchell Brittnacher, Michael Jacobs, Christopher Armour, Matthew Radey, Richard Bunt, Hillary Hayden, Ryland Bydalek, and E. Peter Greenberg “Cross-Species Comparison of the Burkholderia pseudomallei, Burkholderia thailandensis, and Burkholderia mallei Quorum Sensing Regulons” J. Bacteriol. 2014, 196, 22, 3862.

Charlotte Majerczyk, Mitchell Brittnacher, Michael Jacobs, Christopher D. Armour, Mathew Radey, Emily Schneider, Somsak Phattarasokul, Richard Bunt and E. Peter Greenberg “Global Analysis of the Burkholderia thailandensis Quorum Sensing-Controlled Regulon” J. Bacteriol. 2014, 196, 7, 1412.

Charlotte Majerczyk, Loren Kinman, Tony Han, Richard Bunt, and E. Peter Greenberg “Virulence of Burkholderia mallei Quorum-Sensing Mutants” Infect. Immun. 2013, 81, 5, 1471.

Vasiliou, A.K.; Kim, J.; Ormond,T.; Piech, K.; Urness, K.; Sheer, A.; Robichaud, D.; Mukarakate, C.; Nimlos, M.R.; Daily, J.W.; Gaun, Q.; Carstensen, H.H.; Ellison.G.B. Biomass pyrolysis: Thermal decomposition mechanism of furfural and benzaldehyde. Journal of Chemical Physics, 2013, 139, 104310.

*Wolf, M.W.; Choi, S. "Disproportionation of Pentaammineruthenium(III)-Nucleoside Complexes Leads to Two-Electron Oxidation of Nucleosides without Involving Oxygen Molecules" J. Bio. Inorg. 2012, 17, 1283-1291, DOI 10.1007/s00775-012-0942-8.

Costanza-Robinson, M. S., *Zheng, Z., Henry, E. J., *Estabrook, B. D., *Littlefield, M. H. Implications of surfactant-induced flow for miscible-displacement estimation of air-water interfacial areas in unsaturated porous media. Environmental Science and Technology 2012, 46, 11206-11212, doi:10.1021/es303003v.

Vasiliou, A.; Piech, K.; Zhang, X.; Reed, B.; Nimlos, M. R.; Ahmed, M.; Golan, A.; Kostco, O.; Osborn, D. L.; David, D.E.; Urness, K.N.; Daily, J. W.; Stanton, J. F.; Ellison, G. B “Thermal decomposition of CH3CHO studied by matrix infrared spectroscopy and photoionization mass spectroscopy,” Journal of Chemical Physics, 2012, 137, 164308.

Paul B. Armstrong, *Elizabeth A. Dembicer, *Andrew J. DesBois, *Jay T. Fitzgerald, *Janet K. Gehrmann, *Nathaniel C. Nelson, *Amelia Noble and Richard C. Bunt “Investigation of the Electronic Origin of Asymmetric Induction in Palladium-Catalyzed Allylic- Substitutions with Phosphinooxazoline (PHOX) Ligands by Hammett and Swain−Lupton Analysis of the 13C NMR Chemical Shifts of the p-Allylpalladium Intermediates,” Organometallics 2012, 31, 6933.

*Hildick-Smith GJ, *Downey MC, *Gretebeck LM, *Gersten RA, Sandwick RK. “Ribose 5-phosphate glycation reduces cytochrome c respiratory activity and membrane affinity.” Biochemistry. 2011, 50, 11047-57. doi: 10.1021/bi2012977.

*Bokiej M, *Livermore AT, *Harris AW, *Onishi AC, Sandwick RK.”Ribose sugars generate internal glycation cross-links in horse heart myoglobin.” Biochem Biophys Res Commun. 2011, 407, 191-6. doi: 10.1016/j.bbrc.2011.02.138.

Vasiliou, A.; Piech, K.; Zhang, X.; Reed, B.; Nimlos, M. R.; Ahmed, M.; Golan, A.;Kostco, O.; Osborn, D. L.; Daily, J. W.; Stanton, J. F.; Ellison, G. B. The Products of Thermal Decomposition of CH3CHO. Journal of Chemical Physics: Communication, 2011, 135.

Choi, S.; *Ryu, DW; *DellaRocca, JG; *Wolf, M. W.; *Bogart, J. A. "Two Electron Oxidation of             Deoxyguanosine by a Ru(III) Complex without Involving Oxygen Molecules through             Disproportionation" Inorg. Chem. 2011, 50, 6567-6574.

Choi, S.; *Personick M. L.; *Bogart, J. A.; *Ryu, DW; *Redman, R. M.; *Laryea-Walker, E. "Oxidation of a Guanine Derivative Coordinated to a Pt(IV) Complex Initiated by Intermolecular Nucleophilic Attacks" Dalton Trans. 2011, 40, 2888-2897.

Jewett, K., Sandwick, R.K. Ribose “5-Phosphate Isomerase Investigations for the Undergraduate Biochemistry Laboratory” J. Chem. Ed., 2011, 88, 1170-1174. doi: 10.1021/ed100670a

*Gersten RA, *Gretebeck LM, *Hildick-Smith G, Sandwick RK. “Maillard reaction of ribose 5-phosphate generates superoxide and glycation products for bovine heart cytochrome c reduction.” Carbohydr Res. 2010, 345, 2499-506. doi: 10.1016/j.carres.2010.09.013.

Larrabee, J. A.; *Johnson, W. R.; *Volwiler, A. S. "Magnetic Circular Dichroism Study of a Complex with Mixed 5- and 6-Corrdination: A Spectroscopic Model for Dicobalt(II) Hydrolases." Inorganic Chemistry 2009, 48, 8822-8829.

Larrabee, J. A.; *Chyun, S-A.; *Volwiler, A. S. "Magnetic Circular Dichroism Study of a Methionine Aminopeptidase/Fumagillin Complex and Dicobalt II-II and II-III Model Complexes" Inorganic Chemistry2008, 47, 10499-10508.

Hadler, K. S.; Tanifum, E.; Yip, S. H-C.; Mitic, N.; Guddat, L. W.; Jackson, C. J.; Gahan, L. R.; Carr, P.; Ollis, D. L.; Hengge, A. C.; Larrabee, J. A.; Schenk, G. "Substrate Induced Formation of a Catalytically Competent Binuclear Center and Regulation of Reactivity in Glycerophosphodiesterase from Enterobacter aerogenes" Journal of the American Chemical Society 2008, 130, 14129-14138.

Johansson, F. B.; Bond, A. D.; Nielsen, U. G.; Moubaraki, B.; Murray, K. S.; Berry, K. J.; Larrabee, J. A.; McKenzie, C. J. "Dicobalt II-II, II-III and III-III Complexes as Spectroscopic Models for Dicobalt Enzyme Active Sites" Inorganic Chemistry 2008, 47, 5079-5092.

Robinson, M. S.; Stoller, F. L.; Costanza-Robinson, M. S.; Jones, J. K. Write Like a Chemist: A Guide and Resource. Oxford University Press: New York, 2008.

Choi, S.; Vastag, L.; Larrabee, Y. C.;* Personick, M. L.;* Schaberg, K. B.;* Fowler, B. J.;* Sandwick, R. K.; Rawji, G. "The Importance of Pt(II) Catalyzed Pt(IV) Substitution for the Oxidation of Guanosine Derivatives by Pt(IV) Complexes" Inorg. Chem., 2008, 47, 1352-1360. Correction: Inorg. Chem., 2008, 47, 3920-3920.

Costanza-Robinson, M. S.; Harrold, K.H.*; Lieb-Lappen, R.M.*; X-ray Microtomography Determination of Air-Water Interfacial Area-Water Saturation Relationships in Sandy Porous Media. Environmental Science and Technology, 2008, 42, 2949-2956.

Byers, J. H.*; Neale, N. R.*; Alexander, J. B.* Gangemi, S. P.* "Radical Aromatic Substitution with Benzene Chromiumtricarbonyl" Tetrahedron Lett. 2007, 48, 7903-7905.

Byers, J. H.; Goff, P. H.*; Janson, N. J.*; Mazzotta, M. G.*; Swigor, J. E. "The Radical Addition of Dimethyl 2-Ethynylcyclopropane-1,1-dicarboxylate to Electron-Rich Olefins" Synthetic Communications, 2007, 37, 1865-1871.

Munanairi, A.*; O’Banion, S.K.*; Gamble, R.*; Breuer, E.*; Harris, A.W.*; & Sandwick, R.K.  “The multiple Maillard reactions of ribose and deoxyribose sugars and sugar phosphates” Carbohydr. Res. 2007, 342, 2575 – 2592

Brusseau, M. L.; Peng, S.; Schnaar, G.; Costanza-Robinson, M. S. Relationships among air-water interfacial area, capillary pressure, and water saturation for a sandy porous medium. Water Resources Research, 2006, 42, W03501, doi:10.1029/2005WR004058.

Choi, S.; Vastag, L.*; Leung, C. H.*; Beard, A. M.*, Knowles, D. E.*, Larrabee, J. A. "Kinetics and Mechanism of Oxidation of Guanosine Derivatives by Platinum(IV) Complexes" Inorg. Chem., 2006, 45, 10108-10114.

Byers, J. H.; Janson, N. J.* "Radical Additions to (n6-Styrene) Chromium Tricarbonyl" Organic Letters, 2006, 8, 3453.

Byers, J.H. "Thiocarbonyldiimidazole" Encyclopedia of Reagents for Organic Synthesis, L. A. Paquette, Ed. Wiley, 2006.

Byers, J. H.; Sontum, S. F.; Dimitrova, T. S.*; Huque, S.*; Zhang, Y.*; Zegarelli, B. M.*; Jasinski, J. P; Butcher, R. P. Radical Reactions Mediated by Cyclobutadieneiron Tricarbonyl, Organometallics 2006, 25, 3787.

Brusseau, M. L.; Peng, S.; Schnaar, G.; Costanza-Robinson, M. S. Relationships among air-water interfacial area, capillary pressure, and water saturation for a sandy porous medium. Water Resources Research, 2006, 42, W03501, doi:10.1029/2005WR004058.

Stoller, F. L.; Jones, J. K.; Costanza-Robinson, M. S.; Robinson, M. S. Demystifying disciplinary writing: A case study in the writing of chemistry. Language and Learning Across the Disciplines 2005, May 15.

Paul B. Armstrong,* Lisa M. Bennett, Ryan N. Constantine,* Jessica L. Fields,* Jerry P. Jasinski, Richard J. Staples, Richard C. Bunt "Hammett 13C NMR and X-ray studies of allylpalladium phosphinooxazoline chiral ligand complexes", Tetrahedron Lett. 2005, 46, 1441-1445.

Sandwick, R., Johanson, M.* and Breuer, E.*  "Maillard Reactions of Ribose 5-Phosphate and Amino Acids" in The Maillard Reaction: Chemistry at the Interface of Nutrition, Aging, and Disease, Baynes, J., Monnier, V.M., Ames, J.M., and Thorpe, S.R. (eds), Annals of the New York Academy of Sciences 2005, New York, 1043, 85 - 96.

Choi, S.; Cooley, R. B.*; Voutchkova, A.*; Leung, C. H.*; Vastag, L.*; Knowles, D. E.* "Oxidation of Guanosine Derivatives by a Platinum(IV) Complex: Internal Electron Transfer through Cyclization" J. Am. Chem. Soc, 2005, 127, 1773-1781.

Sandwick, R., Johanson, M.* and Breuer, E.*  "Maillard Reactions of Ribose 5-Phosphate and Amino Acids" in The Maillard Reaction: Chemistry at the Interface of Nutrition, Aging, and Disease, Baynes, J., Monnier, V.M., Ames, J.M., and Thorpe, S.R. (eds), Annals of the New York Academy of Sciences 2005, New York, 1043, 85 - 96.

Byers, J. H.; DeWitt, A.*; Nasveschuk, C. G.*; Swigor, J. E.  "Tandem Radical-Electrophilic Annulations to Pyrrole" , Tetrahedron Lett., 2004, 45,6587-6590.

Sunhee Choi, Richard B. Cooley,* Amanda S. Hakemian,* Yuna C. Larrabee, Richard C. Bunt, Stéphane D. Maupas, James G. Muller, and Cynthia J. Burrows, "Mechanism of Two-Electron Oxidation of Deoxyguanosine 5'-Monophosphate by a Platinum(IV) Complex" J. Am. Chem. Soc. 2004, 126, 591.

Cluss, R. G., Silverman*, D. A., and T. R. Stafford*. 2004. Extracellular secretion of the Borrelia burgdorferi Oms28 Porin and Bgp, a glycosaminoglycan binding protein. Infect. Immun. 62:6279-6286.

Ryan N. Constantine,* Naomi Kim,* and Richard C. Bunt, "Hammett Studies of Enantiocontrol by PHOX Ligands in Pd-Catalyzed Allylic Substitution Reactions" Org. Lett. 2003, 5, 2279.

Meola,M*, Yamen,B.*, Weaver,K.*, and Sandwick,RK. "The Catalytic Effect of Mg2+ and Imidazole on the Decomposition of 5-Phosphoribosyl-a-1-pyrophosphate in Aqueous Solution" J. Inorg. Biochem.2003, 93, 235 - 242

Byers, J. H.; Duff, M. P.*; Woo, G. W.* "A One-Step Radical Synthesis of Pyrrol-2-Acetic Acids", Tetrahedron Lett., 2003, 44,6853-6855.

Byers, J. H.; Zhang, Y.* "Syntheses of 3-Acylindoles via the Alkylation of the Dianion of 3-Acetylindole"; Heterocycles, 2002, 57, 1293-1297.

Byers, J. H.; Kosterlitz, J. A*.; Steinberg, P. L*. "Tandem Radical Addition Reactions to Substituted Indoles under Atom-Transfer and Oxidative Conditions "; C. R. Acad. Sci., Paris, Chemistry, 2001, 4, 471-476.

Choi, S.; Delaney, S.*; Orbai, L.*; Padgett, E. J.*; Hakemian, A. S.* "A Platinum(IV) Complex Oxidizes   Guanine to 8-Oxo-Guanine in DNA and RNA"  Inorg.Chem., 2001, 40, 5481-5482.

Dennis, A.*, Puskas, M.*, Stasaitis, S.*, and Sandwick, R.K. "The Formation of a 1-5 Phosphodiester Linkage in the Spontaneous Breakdown of 5-Phosphoribosyl-a-1-Pyrophosphate", J. Inorg. Biochem., 2000, 81, 73 - 80.

Choi, S.; Delaney, S.*; Jewett, K. J.*; Orbai, L.* "Reaction of Platinum(IV) Anticancer Complexes with   DNA" J. Inorg. Biochem., 1999, 74, 98-98.

Choi, S.; Mahalingaiah, S.;* Delaney, S.;* Neale,N. R.;* Masood, S.* "Kinetic and Mechanistic Studies of Platinum(IV) Complexes Binding to Guanosine 5'-Monophosphate (5'-GMP)", Inorg. Chem. 1999, 38, 1800-1805.

Larrabee, J. A., *Thamrong-nawasawat, T. *, Mon, S. Y.* "An HPLC Method for the Assay of Methionine Aminopeptidase Activity: Application to the Study of Enzymatic Inactivation", Anal. Biochem., 1999, 269, 194-198.

Byers, J. H.; Campbell, J. E.*; Knapp, F. H.*; Thissell, J. G.*, "Radical Aromatic Substitution via Atom-Transfer Addition" Tetrahedron Lett., 1999, 40, 2677.

Byers, J. H.; Shaughnessy, E. I.*; Mackie, T. N.* "Radical Lactonizations at Anomalously High Concentrations" Heterocycles 1998, 48, 2071.

Sunhee Choi, Catherine Filotto*, Mark Bisanzo,* Sarah Delaney*, Daniel Lagasee*, Jennifer Whitworth*, Andrew Jusko*, Chengruo Li*, Nicole Wood*, Jennifer Willingham*, Amy Schwenker*, and Kathleen Spaulding* "Reduction and Anticancer Activity of Platinum(IV) Complexes", Inorg. Chem. 1998, 37, 2500-2504.

Barry M. Trost and Richard C. Bunt "On the Effect of the Nature of Ion Pairs as Nucleophiles in a Metal Catalyzed Substitution Reaction," J. Am. Chem. Soc. 1998, 120, 70.

Larrabee, J. A.; Alessi, C. M.*; Asiedu, E. T.*; Cook, J. O.*; Hoerning, K. R.*; Klingler, L. J.*; Okin, G. S.*; Santee, S. G.*; Volkert, T. L.* "Magnetic Circular Dichroism Spectroscopy as a Probe of Geometric and Electronic Structure of Cobalt(II)-Substituted Proteins: Ground State Zero Field Splitting as a Coordination Number Indicator", J. Am. Chem. Soc., 1997, 119, 4182-4196.

Byers, J. H.; O'Leary, B. M.*; Zraly, M. A.* "A Novel Radical-Based Synthesis of Valerolactones", Synthetic Commun., 1996, 26, 4039.

Byers, J. H.; Whitehead, C.C.*; Duff, M. E.* "Addition of a Sulfur-Stabilized Radical to Electron-Deficient Alkenes via Phenyl Selenide Transfer", Tetrahedron Lett.1996, 37, 2743.

Barry M. Trost, A. Chris Kruger, Richard C. Bunt, and Jorge Zambrano "On the Question of Asymmetric Induction with Acyclic Allylic Substrates. An Asymmetric Synthesis of (+)‑Polyoxamic Acid," J. Am. Chem. Soc. 1996, 118, 6520.

Barry M. Trost and Richard C. Bunt "On the Question of the Symmetry of Formally Symmetrical π‑(Allyl)palladium Cationic Intermediates in Allylic Alkylations," J. Am. Chem. Soc. 1996, 118, 235.

Barry M. Trost and Richard C. Bunt "On Ligand Design for Outer Sphere Catalytic Reactions. A Simple Asymmetric Synthesis of Vinylglycinol," Angew.Chem., Int. Ed. Engl. 1996, 35, 99.

Cluss, R.G., A. S. Goel*, H. Rehm*, J. G. Schoenecker* and J.T. Boothby. "Coordinate Synthesis and Turnover of Heat Shock Proteins in Borrelia burgdorferi: Degradation of DnaK During Recovery from Heat Shock", Infection and Immunity. 1996, 64, 1736-1743.

Byers, J. H.; Thissell, J. G.*; Thomas, M. A. "The Synthesis of Geminal Diphosphonates via Phenyl Selenide Transfer", Tetrahedron Lett. 1995, 36, 6403-6406.

Byers, J. H.; Thissell, J. G.* "The Photochemical Disproportionation of Dialkyl 2,2-Di(phenylseleno) Malonate", Tetrahedron Lett. 1995, 25, 21-26.

Choi, S.; Swanson, J. M.* "Interaction of cytochrome c with cardiolipin: An Infrared Spectroscopic Study", Biophys.Chem., 1995, 54, 271-278.

Bruck, D.K., M.L. Talbot*, R.G. Cluss, and J. T. Boothby "Ultrastructural Characterization of the Stages of Spheroplast Preparation of Borrelia burgdorferi", J. Microbiological Methods. 1995, 23 (2):219-228.

Barry M. Trost, Richard C. Bunt, and Shon R. Pulley "On the Use of O‑Methylmandelic Acid for the Establishment of Absolute Configuration of a‑Chiral Primary Amines," J. Org. Chem. 1994, 59, 4202.

Barry M. Trost and Richard C. Bunt "Asymmetric Induction in Allylic Alkylations of 3‑Acyloxycycloalkenes," J. Am. Chem. Soc.1994, 116, 4089.


Department of Chemistry & Biochemistry

McCardell Bicentennial Hall
276 Bicentennial Way
Middlebury College
Middlebury, VT 05753