Benjamin C. Gorske

Assistant Professor of Chemistry and Biochemistry

Teaching this semester

CHEM 1060. Chemistry and the Quest for Discovery

An exploration of the nature and evolution of the scientific discovery process as viewed through the lens of important historical and contemporary innovations in the field of chemistry. Examines relationships between cultural context and the motivation, practice, and impact of scientific research. Assumes no background in science. Students participate in weekly laboratory discovery experiences. Not open to students who have credit for a chemistry course numbered 1090 or above.

CHEM 2260. Organic Chemistry II, B

Continuation of the study of the compounds of carbon. Highlights the reactions of aromatic, carbonyl-containing, and amine functional groups. Mechanistic reasoning provides a basis for understanding these reactions. Skills for designing logical synthetic approaches to complex organic molecules are developed. Lectures, review sessions, and four hours of laboratory work per week.

Education

  • Ph.D., Organic Chemistry, University of Wisconsin–Madison, ; Madison, WI, 2007
  • B.A., Chemistry, Lawrence University; Appleton, WI, 1995
  • B.M., Piano Performance, Lawrence University; Appleton, WI, 1995

Publications

“A Peptoid Square Helix via Synergistic Control of Backbone Dihedral Angles.” Gorske, B. C.*; Mumford, E. M.; Gerrity, C. G.; Ko, I. J. Am. Chem. Soc. 2017, 139, 8070–8073.

“Tandem Incorporation of Enantiomeric Residues Engenders Discrete Peptoid Secondary Structures.” Gorske, B. C.*; Mumford, E. M.; Conry, R. C. Org. Lett. 2016, 18, 2780–2783.

“Bridged n®p* Interactions Can Stabilize Peptoid Helices.” Gorske, B. C.*; Nelson, R. C.; Bowden, Z. S.; Kufe, T. A.; Childs, A. M. J. Org. Chem. 2013, 78, 11172–11183.

“New Strategies for the Design of Folded Peptoids Revealed by a Survey of Noncovalent Interactions in Model Systems.” Gorske, B. C.; Stringer, J. R.; Bastian, B. L.; Fowler, S. A.; Blackwell, H. E. J. Am. Chem. Soc. 2009, in press.

“Regio- and Stereoselective Synthesis of Fluoroalkenes by Directed Au(I) Catalysis.” Gorske, B. C.; Mbofana, C. T.; Miller, S. J. Org. Lett. 200911, 4318-4321.

“Local and Tunable n®p* Interactions Regulate Amide Isomerism in the Peptoid Backbone.” Gorske, B. C.; Bastian, B. L.; Geske, G. D.; Blackwell, H. E. J. Am. Chem. Soc. 2007129, 8928-8929.

Highlighted by Faculty of 1000 Biology (Faculty of 1000 Biology: evaluations for Gorske BC et al J Am Chem Soc 2007 Jul 25 129 (29) :8928-9 http://www.f1000biology.com/article/id/1088560/evaluation)

“Tuning Peptoid Secondary Structure with Pentafluoroaromatic Functionality: A New Design Paradigm for the Construction of Discretely Folded Peptoid Structures.” Gorske, B. C.; Blackwell, H. E. J. Am. Chem. Soc.2006128, 14378-14387.

Highlighted as a Tech Advance by Faculty of 1000 Biology (Faculty of 1000 Biology: evaluations for Gorske BC & Blackwell HE J Am Chem Soc 2006 Nov 8 128 (44) :14378-87 http://www.f1000biology.com/article/id/1050425/evaluation)

“Interception of Quorum Sensing in Staphylococcus aureus: A New Niche for Peptidomimetics.” Gorske, B. C.; Blackwell, H. E. Org. Biomol. Chem. 20064, 1441-1445.

N-[1-(Pentafluorophenyl)ethyl]acetamide.” Guzei, I. A.; Gorske, B. C.; Blackwell, H. E. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 200662, o286-o288.

“Expedient Synthesis and Design Strategies for New Peptoid Construction.” Gorske, B. C.; Jewell, S. A.; Guerard, E. J.; Blackwell, H. E. Org. Lett. 20057, 1521-1524.

Presentations and Proceedings

1. “New Methods to Control Peptoid Secondary Structure using Electronically Deactivated and Sterically Hindered Amide Side Chains.” Sarah A. Fowler, Benjamin C. Gorske, and Helen E. Blackwell. Poster presented at the 233rd ACS National Meeting, Chicago, IL, March 2007; ORGN 635.

2. "Microwave-Assisted Syntheses of Peptoids and Peptomers toward the Development of Novel

Quorum Sensing Modulators." Fowler, S. A.; Gorske, B. C.; Bastian, B. L.; Blackwell, H. E. Poster presented at the Pfizer Diversity in Organic Chemistry Symposium, Pfizer Global R&D, Groton, CT, October 2006.

3. “Tuning Peptoid Secondary Structure with Pentafluoroaromatic Functionality: A New Design Paradigm for the Construction of Discretely Folded Peptoid Structures.” Gorske, B. C.; Blackwell, H. E. Poster presented at the American Chemical Society 232nd National Meeting and Exposition, San Francisco, CA, September 2006.

4. “Tuning Noncovalent Interactions to Control Peptoid Structure.” Gorske, B. C.; Blackwell, H. E. Talk presented at the 5th Peptoid Summit, Berkeley, CA, September 2006.

5. “Microwave-Assisted Syntheses of Peptoids and Peptomers: Investigations toward Defined Structure and Biological Function.” Fowler, S. A.; Gorske, B. C.; Bastian, B. L.; Blackwell, H. E. Poster presented at the Medicinal Chemistry Gordon Research Conference, Colby-Sawyer College, New London, NH, August 2006. *Awarded “Best Poster” prize.

6. “Microwave-Assisted Synthesis of Peptoids and Peptomers: Investigations toward Defined Structure and Biological Function.” Jewell, S. A.; Gorske, B. C.; Blackwell, H. E. Poster presented at the 4th International Microwaves in Chemistry Conference, Orlando, FL, March 2006.

7. “Microwave-Assisted Peptoid Synthesis: New Paradigms for Peptidomimetic Architecture.” Gorske, B. C.; Jewell, S. A.; Guerard, E. J.; Blackwell, H. E. Poster presented at the 4th Peptoid Summit Conference, Northwestern University, Evanston, IL, June 2005.

8. “Microwave-Assisted Peptoid Synthesis: New Paradigms for Peptidomimetic Architecture.” Gorske, B. C.; Jewell, S. A.; Guerard, E. J.; Blackwell, H. E. Poster presented at the 3rd International Microwaves in Chemistry Conference, Orlando, FL, March 2005.

9. “Chemical Approaches for Drug Delivery.” Gorske, B. C. Talk presented to the UW – Madison Chemistry Department, Madison, WI, February 2005.

10. “Reinventing Solid-Phase Combinatorial Synthesis through Microwave-Assisted Organic Reactions.” Bowman, M. D.; Lin, Q.; Gorske, B. C.; Geske, G. D.; Blackwell, H. E. Talk presented at the Strategic Research Institute's Microwaves for Organic Synthesis Conference, Boston, MA, November 2004.

11. “New Strategies for Parallel Library Synthesis.” Bowman, M. D.; Lin, Q.; Gorske, B. C.; Blackwell, H. E. Poster presented at the 3rd German-American Symposium on the Frontiers of Chemistry, Kloster Seeon, Germany, July 2004.