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Biomimetic Architectures

Butterfoss, G. L.; Yoo, B.; Jaworski, J. N.; Chorny, I.; Dill, K. A.; Zuckermann, R.; Bonneau, R.; Kirshenbaum, K.; Voelz, V. A. (2012) De novo structure prediction and experimental characterization of folded peptoid oligomers. Proc. Natl. Acad. Sci. USA. 109(36): 14320-14325. HTML/PDF

Vollrath, S. B. L.; Brase, S.; Kirshenbaum, K. Twice Tied Tight: Enforcing Conformational Order in Bicyclic Peptoid Oligomers. (2012) Chemical Science 3: 2726-2731. HTML/PDF

Paul, B.; Butterfoss, G. L.; Boswell, M. G.; Huang, M. L.; Bonneau, R.; Wolf, C.; Kirshenbaum, K. (2012) N-Naphthyl peptoid foldamers exhibiting atropisomerism. Org Lett 14: 926-929. HTML/PDF

Jordan, P. A.; Paul, B.; Butterfoss, G. L.; Renfrew, P. D.; Bonneau, R.; Kirshenbaum, K. (2011) Oligo(N-alkoxy glycines): Trans substantiating peptoid conformations. Biopolymers (Pept. Sci.) 96: 617-626. HTML/PDF

Paul, B.; Butterfoss, G. L.; Boswell, M. G.; Renfrew, P. D.; Yeung, F. G.; Shah, N. H.; Wolf, C.; Bonneau, R.; Kirshenbaum, K. (2011) Peptoid atropisomers. J. Am. Chem. Soc. 133: 10910-10919. HTML/ PDF

Yoo, B.; Shin, S. B. Y.; Huang, M. L.; Kirshenbaum, K. (2010) Peptoid Macrocycles: Making the Rounds with Peptidomimetic Oligomers. Chem. Eur. J. 16: 5528-5537. HTML/ PDF

Holub, J. M.; Kirshenbaum, K. (2010) Tricks with Clicks: Modification of Peptidomimetic Oligomers via Copper-catalyzed Azide-alkyne [3+2] Cycloaddition. Chem. Soc. Rev. 39: 1325-1337. HTML/ PDF

Butterfoss, G. L.; Renfrew, P. D.; Kuhlman, B.; Kirshenbaum, K.; Bonneau, R. (2009) A Preliminary Survey of the Peptoid Folding Landscape. J. Am. Chem. Soc. 131: 16798- 16807. HTML/ PDF

Jagasia, R.; Holub, J. M.; Bollinger, M.; Kirshenbaum, K.; Finn, M.G. (2009) Peptide Cyclization and Cyclodimerization by CuI-Mediated Azide-Alkyne Cycloaddition. J. Org. Chem. 74: 2964-2974. HTML/ PDF

Maayan, G.; Ward, M.; Kirshenbaum, K. (2009). Metallopeptoids. Chem. Commun. 56-58. HTML / PDF

Yoo, B.; Kirshenbaum, K. (2008). Peptoid Architectures: Elaboration, Actuation, and Application. Curr. Opin. Chem. Biol. 12: 1-8. HTML / PDF

Shah, N. H.; Butterfoss, G. L.; Nguyen, K.; Yoo, B.; Bonneau, R.; Rabenstein, D. L.; Kirshenbaum, K. (2008). Oligo(N-aryl glycines): A New Twist on Structured Peptoids. J. Am. Chem. Soc. 130: 166222-16632. HTML / PDF

Shah, N.H.; Kirshenbaum, K. (2008). Photoresponsive Peptoid Oligomers Bearing Azobenzene Side Chains. Org. Biomol. Chem. 6: 2516-2521. HTML / PDF

Maayan, G.; Yoo, B.; Kirshenbaum, K. (2008). Heterocyclic Amines for the Construction of Peptoid Oligomers Bearing Multi-Dentate Ligands. Tet. Lett. 49: 335-338. HTML / PDF

Shin, S.-B.Y.; Kirshenbaum, K. (2007). Conformational Rearrangements by Water-Soluble Peptoid Foldamers. Org. Lett., 9: 5003-5006. HTML / PDF

Jang, H.J., Fafarman, A., Holub, J.M., Kirshenbaum, K. (2005). Click to fit: Versatile polyvalent display on a peptidomimetic scaffold. Org. Let. 7: 1951-1954. HTML / PDF

Yoo, B., Kirshenbaum, K. (2005). Protease-mediated ligation of abiotic oligomers. J. Am. Chem. Soc. 127: 17132-17133. HTML / PDF

Huang, K., Wu, C.W., Sanborn, T.J., Patch, J.A., Kirshenbaum, K., Zuckermann, R.N., Barron, A.E., Radhakrishnan, I. (2006). A threaded loop conformation adopted by a family of peptoid nonamers. J. Am. Chem. Soc. 128: 1733-1738. HTML / PDF

Holub, J.M., Jang, H., Kirshenbaum, K. (2006). Clickity-click: Highly functionalized peptoid oligomers generated by sequential conjugation reactions on solid-phase support. Org. Biomol. Chem. 4: 1497-1502. HTML / PDF

Fafarman, A.T., Borbat, P.P., Freed, J.H., Kirshenbaum, K. (2007). Characterizing the structure and dynamics of folded oligomers: Pulsed ESR studies of peptoid helices. Chem. Commun. 2: 377-379. HTML / PDF

Holub, J.M., Jang, H., Kirshenbaum, K. (2007). Fit To Be Tied: Conformation-Directed Macrocyclization of Peptoid Foldamers. Org. Lett. 9: 3275-3278. HTML / PDF

Shin, S.-B.Y., Yoo, B., Todaro, L., Kirshenbaum, K. (2007). Cyclic Peptoids. J. Am. Chem. Soc. 129: 3218-3225. HTML / PDF

Holub, J.M., Jang, H., Kirshenbaum, K. (2006). Clickity-click: Highly functionalized peptoid oligomers generated by sequential conjugation reactions on solid-phase support. Org. Biomol. Chem. 4: 1497-1502. HTML / PDF

Huang, K., Wu, C.W., Sanborn, T.J., Patch, J.A., Kirshenbaum, K., Zuckermann, R.N., Barron, A.E., Radhakrishnan, I. (2006). A threaded loop conformation adopted by a family of peptoid nonamers. J. Am. Chem. Soc. 128: 1733-1738. HTML / PDF

Jang, H.J., Fafarman, A., Holub, J.M., Kirshenbaum, K. (2005). Click to fit: Versatile polyvalent display on a peptidomimetic scaffold. Org. Let. 7: 1951-1954. HTML / PDF

Yoo, B., Kirshenbaum, K. (2005). Protease-mediated ligation of abiotic oligomers. J. Am. Chem. Soc. 127: 17132-17133. HTML / PDF

Biomedical Applications of Peptidomimetics

Levine, P. M.; Lee, E.; Greenfield, A.; Bonneau, R.; Logan, S. K.; Garabedian, M. J.; Kirshenbaum, K. (2012) Androgen Receptor Antagonism by Divalent Ethisterone Conjugates in Castrate-Resistant Prostate Cancer Cells. ACS Chem. Biol. 7: 1693-1701. HTML/PDF

Levine, P. M.; Imberg. K; Garabedian, M. J.; Kirshenbaum, K. (2012) Multivalent Peptidomimetic Conjugates: A Versatile Platform For Modulating Androgen Receptor Activity.  J. Am. Chem. Soc. 134: 6912-6915. HTML/PDF

Huang, M. L.; Shin, S. B. Y.; Benson, M. A.; Torres, V. J.; Kirshenbaum, K. (2012) A comparison of linear and cyclic peptoid oligomers as potent antimicrobial agents. ChemMedChem 7: 114-122. HTML/PDF

Holub, J. M.; Garabedian, M. J.; Kirshenbaum, K. (2011) Modulation of human estrogen receptor α activity by multivalent estradiol-peptidomimetic conjugates. Mol. BioSyst. (2011) 7: 337-345. link

Utku, Y., Dehan, E., Ouerfelli, O., Piano, F., Zuckermann, R.N., Pagano, M., Kirshenbaum, K. (2006). A peptidomimetic siRNA transfection reagent for highly effective gene silencing. Mol. BioSystems. 2: 312-317. HTML / PDF

Holub, J. M., Garabedian, M.J., Kirshenbaum, K. (2007). Peptoids on Steroids: Precise Multivalent Estradiol-Peptidomimetic Conjugates Generated via Azide-Alkyne [3+2] Cycloaddition Reactions. QSAR & Comb. Sci. 26: 1175-1180. PDF

Bionanotechnology and Materials

Huang, M.; Ehre, D.; Jiang, Q.; Hu, C.; Kirshenbaum, K.; Ward. M. (2012) Biomimetic Peptoid Oligomers as Dual-Action Antifreeze Agents. PNAS 109, 49: 19922-19927. HTML/PDF

Maayan, G. Ward, M.; Kirshenbaum, K. (2009) Folded Biomimetic Oligomers for Enantioselective Catalysts. Proc. Natl. Acad. Sci. USA 106: 13679-13684. PDF

Shah, N.H.; Kirshenbaum, K. (2008). Direct Generation of Polymer Films on Copper Surfaces Through Azide-Alkyne Cycloaddition Reactions Between Peptidomimetic Oligomers. Macromol. Rapid Commun. 29: 1134-1139. HTML / PDF

Arora, P.S., Kirshenbaum, K. (2004). Nano-tailoring: Stitching alterations on viral coats. Chem. Biol. 11: 418-420. HTML / PDF

Anderson, E.A., Isaacman, S., Peabody, D.S., Wang, E.Y., Canary, J.W., Kirshenbaum, K. (2006). Viral nanoparticles donning a paramagnetic coat: conjugation of MRI contrast agents to the MS2 capsid. NanoLetters. 6: 1160-1164. HTML / PDF

Education

Pohl, N. L. B.; Kirshenbaum, K.; Yoo, B.; Schulz, N.; Zea, C. J.; Streff, J. M.; Schwarz, K. L. (2011) Student-driven design of peptide mimetics: microwave-assisted synthesis of peptoid oligomers. J. Chem. Ed. 88: 999-1001. HTML/ PDF

Johnson, A. ; Kirshenbaum, K.; McBride, A. E. "Designing a Sustainable and Stretchable 'Fox Testicle' Ice Cream", invited chapter in The Kitchen as Laboratory; Vega, C.; Ubbink, J; van der Linden, E.; Columbia University Press, New York, 2012.

Spencer, T., Yoo, B., Kirshenbaum, K. (2006). Purification and modification of fullerene C60 in the undergraduate laboratory. J. Chem. Ed. 83: 1218-1220. PDF