Caroline Proulx

Galiakhmetov, A. R., Shah, A. A., Lane, A., Davern, C. M., Proulx, C., & Nevzorov, A. A. (2024). Peptoid-based macrodiscs of variable lipid composition for structural studies of membrane proteins by oriented-sample solid-state NMR. JOURNAL OF STRUCTURAL BIOLOGY-X, 9. https://doi.org/10.1016/j.yjsbx.2023.100095

Davern, C. M., & Proulx, C. (2023, August 14). Late-Stage Chloride Displacements Enable Access to Peptoids with cis-Inducing Alkylammonium Side Chains. ORGANIC LETTERS, Vol. 8. https://doi.org/10.1021/acs.orglett.3c02393

Galiakhmetov, A. R., Davern, C. M., Esteves, R. J. A., Awosanya, E. O., Guthrie, Q. A. E., Proulx, C., & Nevzorov, A. A. (2022). Aligned peptoid-based macrodiscs for structural studies of membrane proteins by oriented-sample NMR. BIOPHYSICAL JOURNAL, 121(17), 3263–3270. https://doi.org/10.1016/j.bpj.2022.07.024

Bowles, M. O., & Proulx, C. (2022). Late-Stage N-Alkylation of Azapeptides. ORGANIC LETTERS, 24(9), 1768–1773. https://doi.org/10.1021/acs.orglett.2c00046

Young, H. A., & Proulx, C. (2022, May 19). On-resin C alpha-functionalization of N-arylglycinyl peptides with boronic acids. ORGANIC & BIOMOLECULAR CHEMISTRY, Vol. 5. https://doi.org/10.1039/d2ob00524g

Bowles, M., & Proulx, C. (2021). Solid phase submonomer azapeptide synthesis. SYNTHETIC AND ENZYMATIC MODIFICATIONS OF THE PEPTIDE BACKBONE, Vol. 656, pp. 169–190. https://doi.org/10.1016/bs.mie.2021.04.020

Davern, C. M., Lowe, B. D., Rosfi, A., Ison, E. A., & Proulx, C. (2021, May 10). Submonomer synthesis of peptoids containing trans-inducing N-imino- and N-alkylamino-glycines. CHEMICAL SCIENCE, Vol. 5. https://doi.org/10.1039/d1sc00717c

Fregeau, G., Sarduy, R., Elimam, H., Esposito, C. L., Mellal, K., Menard, L., … Marleau, S. (2020). Atheroprotective and atheroregressive potential of azapeptide derivatives of GHRP-6 as selective CD36 ligands in apolipoprotein E-deficient mice. ATHEROSCLEROSIS, 307, 52–62. https://doi.org/10.1016/j.atherosclerosis.2020.06.010

Proulx, C. (2020, May 29). Catching up to nature's ribosomes. SCIENCE, Vol. 368, pp. 941–941. https://doi.org/10.1126/science.abb9711

Young, H. A., Guthrie, Q. A. E., & Proulx, C. (2020). N-Arylation of Amino Acid Esters to Expand Side Chain Diversity in Ketoxime Peptide Ligations. JOURNAL OF ORGANIC CHEMISTRY, 85(3), 1748–1755. https://doi.org/10.1021/acs.joc.9b02810

Reese, H. R., Shanahan, C. C., Proulx, C., & Menegatti, S. (2020). [Review of Peptide science: A "rule model" for new generations of peptidomimetics]. ACTA BIOMATERIALIA, 102, 35–74. https://doi.org/10.1016/j.actbio.2019.10.045

Proulx, C., Zhang, J., Sabatino, D., Chemtob, S., Ong, H., & Lubell, W. D. (2020). [Review of Synthesis and Biomedical Potential of Azapeptide Modulators of the Cluster of Differentiation 36 Receptor (CD36)]. BIOMEDICINES, 8(8). https://doi.org/10.3390/biomedicines8080241

Proulx, C. (2019, November). Aerobic oxidation of N-aryl peptides for catalyst-free oxime ligations. Presented at the Appalachian State University, Boone, NC.

Guthrie, Q. A. E., & Proulx, C. (2019). Aerobic oxidation of N-phenylglycinyl peptides for catalyst-free oxime ligations. American Chemical Society (ACS) meeting. Presented at the American Chemical Society (ACS) meeting, Orlando, Florida.

McMechen, M. A., Willis, E. L., Gourville, P. C., & Proulx, C. (2019). Aza-Amino Acids Disrupt -Sheet Secondary Structures. MOLECULES, 24(10). https://doi.org/10.3390/molecules24101919

Proulx, C. (2019). In situ oxidation of N-phenylglycinyl peptides for oxime bond formation at neutral pH. American Peptide Symposium 2019. Presented at the American Peptide Symposium, Monterey, CA.

Guthrie, Q. A. E., Young, H. A., & Proulx, C. (2019). Ketoxime peptide ligations: oxidative couplings of alkoxyamines to N-aryl peptides. CHEMICAL SCIENCE, 10(41), 9506–9512. https://doi.org/10.1039/c9sc04028e

Proulx, C. (2019). New strategies for Ketoxime peptide ligations. Boulder Peptide Symposium 2019. Presented at the Boulder Peptide Symposium 2019, Boulder, CO.

Proulx, C. (2019, April). Oxime ligation via in situ oxidation of N-phenylglycinyl peptides. Presented at the Seton Hall University, South Orange, NJ.

Huynh, D. N., Bessi, V. L., Menard, L., Piquereau, J., Proulx, C., Febbraio, M., … Marleau, S. (2018). Adiponectin has a pivotal role in the cardioprotective effect of CP-3(iv), a selective CD36 azapeptide ligand, after transient coronary artery occlusion in mice. FASEB JOURNAL, 32(2), 807–818. https://doi.org/10.1096/fj.201700505r

Battigelli, A., Kim, J. H., Dehigaspitiya, D. C., Proulx, C., Robertson, E. J., Murray, D. J., … Zuckermann, R. N. (2018). Glycosylated Peptoid Nanosheets as a Multivalent Scaffold for Protein Recognition. ACS Nano, 12(3), 2455–2465. https://doi.org/10.1021/ACSNANO.7B08018

Guthrie, Q. A. E., & Proulx, C. (2018). Oxime Ligation via in situ Oxidation of N-Phenylglycinyl Peptides. ORGANIC LETTERS, 20(9), 2564–2567. https://doi.org/10.1021/acs.orglett.8b00713

Guthrie, Q. A., & Proulx, C. (2018, February 11). Oxime ligation via in situ oxidation of N-phenylglycinyl peptides. Presented at the Chemistry  and  Biology  of  Peptides  Gordon  Research  Conference  (GRC), Ventura, California.

Chingle, R., Proulx, C., & Lubell, W. D. (2017). [Review of Azapeptide Synthesis Methods for Expanding Side-Chain Diversity for Biomedical Applications]. ACCOUNTS OF CHEMICAL RESEARCH, 50(7), 1541–1556. https://doi.org/10.1021/acs.accounts.7b00114

Robertson, E. J., Battigelli, A., Proulx, C., Mannige, R. V., Haxton, T. K., Yun, L., … Zuckermann, R. N. (2016). Design, Synthesis, Assembly, and Engineering of Peptoid Nanosheets. Accounts of Chemical Research, 49(3), 379–389. https://doi.org/10.1021/ACS.ACCOUNTS.5B00439

Flood, D., Proulx, C., Robertson, E. J., Battigelli, A., Wang, S., Schwartzberg, A. M., & Zuckermann, R. N. (2016). Improved chemical and mechanical stability of peptoid nanosheets by photo-crosslinking the hydrophobic core. Chemical Communications, 52(26), 4753–4756. https://doi.org/10.1039/C6CC00588H

Robertson, E. J., Proulx, C., Su, J. K., Garcia, R. L., Yoo, S., Nehls, E. M., … Zuckermann, R. N. (2016). Molecular Engineering of the Peptoid Nanosheet Hydrophobic Core. Langmuir, 32(45), 11946–11957. https://doi.org/10.1021/ACS.LANGMUIR.6B02735

Proulx, C., Noë, F., Yoo, S., Connolly, M. D., & Zuckermann, R. N. (2016). On-resin N
-terminal peptoid degradation: Toward mild sequencing conditions. Biopolymers, 106(5), 726–736. https://doi.org/10.1002/BIP.22884

Proulx, C., Yoo, S., Connolly, M. D., & Zuckermann, R. N. (2015). Accelerated Submonomer Solid-Phase Synthesis of Peptoids Incorporating Multiple Substituted N-Aryl Glycine Monomers. The Journal of Organic Chemistry, 80(21), 10490–10497. https://doi.org/10.1021/ACS.JOC.5B01449

Proulx, C., Yoo, S., Connolly, M. D., & Zuckermann, R. N. (2015, June). Molecular Engineering of the Peptoid Nanosheet Hydrophobic Core. Presented at the Canadian Society for Chemistry (CSC) meeting, Ottawa, Ontario.

Mannige, R. V., Haxton, T. K., Proulx, C., Robertson, E. J., Battigelli, A., Butterfoss, G. L., … Whitelam, S. (2015). Peptoid nanosheets exhibit a new secondary-structure motif. Nature, 526(7573), 415–420. https://doi.org/10.1038/NATURE15363

Proulx, C., & Lubell, W. D. (2014). Analysis of N-amino-imidazolin-2-one peptide turn mimic 4-position substituent effects on conformation by X-ray crystallography. Biopolymers, 102(1), 7–15. https://doi.org/10.1002/BIP.22327

Robertson, E. J., Olivier, G. K., Qian, M., Proulx, C., Zuckermann, R. N., & Richmond, G. L. (2014). Assembly and molecular order of two-dimensional peptoid nanosheets through the oil–water interface. Proceedings of the National Academy of Sciences, 111(37), 13284–13289. https://doi.org/10.1073/PNAS.1414843111

Proulx, C., Yoo, S., & Zuckermann, R. N. (2014, June 1). Improvements in the Solid-Phase Synthesis of Peptoids Incorporating Weak Nucleophile Submonomers. Presented at the Canadian Society for Chemistry (CSC) meeting, Vancouver, British Columbia.

Proulx, C., Yoo, S., Connolly, M. D., & Zuckermann, R. N. (2014, August 10). Influence of Backbone Flexibility on the Two-dimensional Assembly of Peptoid Nanosheets. Presented at the American Chemical Society (ACS) meeting, San Francisco, California.

Proulx, C., Su, J. K., Yoo, S., Olivier, G. K., Garcia, R. L., Connolly, M. D., … Zuckermann, R. N. (2014, August 25). Molecular Engineering of the Peptoid Nanosheet Hydrophobic Core. Presented at the Annual User Meeting, Berkeley, California.

Zhang, J., Proulx, C., & Lubell, W. D. (2014, June 1). Multi-component Diversity-Oriented Synthesis of Aza-lysine-peptide Mimics. Presented at the Canadian Society for Chemistry (CSC) meeting, Vancouver, British Columbia.

Zhang, J., Proulx, C., Tomberg, A., & Lubell, W. D. (2014). Multicomponent Diversity-Oriented Synthesis of Aza-Lysine-Peptide Mimics. Organic Letters, 16(1), 298–301. https://doi.org/10.1021/OL403297V

Sun, J., Proulx, C., & Zuckermann, R. N. (2014). Precision Sequence Control in Bioinspired Peptoid Polymers. In ACS Symposium Series (pp. 35–53). https://doi.org/10.1021/bk-2014-1170.ch003

Sanii, B., Haxton, T. K., Olivier, G. K., Cho, A., Barton, B., Proulx, C., … Zuckermann, R. N. (2014). Structure-Determining Step in the Hierarchical Assembly of Peptoid Nanosheets. ACS Nano, 8(11), 11674–11684. https://doi.org/10.1021/NN505007U

Proulx, C., Picard, É., Boeglin, D., Pohankova, P., Chemtob, S., Ong, H., & Lubell, W. D. (2012). Azapeptide Analogues of the Growth Hormone Releasing Peptide 6 as Cluster of Differentiation 36 Receptor Ligands with Reduced Affinity for the Growth Hormone Secretagogue Receptor 1a. Journal of Medicinal Chemistry, 55(14), 6502–6511. https://doi.org/10.1021/jm300557t

Proulx, C., & Lubell, W. D. (2012). N-Amino-imidazolin-2-one Peptide Mimic Synthesis and Conformational Analysis. Organic Letters, 14(17), 4552–4555. https://doi.org/10.1021/ol302021n

Lubell, W. D., Ong, H., Proulx, C., Hopewell, R., Beauregard, K., & Garcia-Ramos, Y. (2012). Peptidomimetics Comprising N-Amino Cyclic Urea Residues and Uses Thereof (Provisional Patent No. US 61/655,682).

Garcia-Ramos, Y., Proulx, C., & Lubell, W. D. (2012). Synthesis of hydrazine and azapeptide derivatives by alkylation of carbazates and semicarbazones. Canadian Journal of Chemistry, 90(11), 985–993. https://doi.org/10.1139/v2012-070

Proulx, C., Sabatino, D., Hopewell, R., Spiegel, J., García Ramos, Y., & Lubell, W. D. (2011). Azapeptides and their therapeutic potential. Future Medicinal Chemistry, 3(9), 1139–1164. https://doi.org/10.4155/fmc.11.74

Proulx, C., & Lubell, W. D. (2011, June 25). In search of azapeptide analogs of GHRP-6 with selective affinity for the CD36 vs GHS-R1a receptor: exploiting the reactivity of semicarbazones and aza-propargyl glycine in combinatorial azapeptide synthesis. Poster presented at the American Peptide Symposium (APS), San Diego, California.

Bolduc, O. R., Lambert-Lanteigne, P., Colin, D. Y., Zhao, S. S., Proulx, C., Boeglin, D., … Masson, J.-F. (2011). Modified peptide monolayer binding His-tagged biomolecules for small ligand screening with SPR biosensors. The Analyst, 136(15), 3142. https://doi.org/10.1039/c1an15235a

Sabatino, D., Proulx, C., Pohankova, P., Ong, H., & Lubell, W. D. (2011). Structure–Activity Relationships of GHRP-6 Azapeptide Ligands of the CD36 Scavenger Receptor by Solid-Phase Submonomer Azapeptide Synthesis. Journal of the American Chemical Society, 133(32), 12493–12506. https://doi.org/10.1021/ja203007u

Proulx, C., & Lubell, W. D. (2011). Synthesis of [Azaphenylglycine4]- and [Aza-1-phenyl-2,3-triazole-3-alanine4] Growth Hormone Releasing Peptide-6 and Comparison of their Conformations with [AzaPhe4]GHRP-6. In M. Lebl (Ed.), Peptides: Building Bridges. Proceedings of the 22nd American Peptide Symposium (pp. 80–81). San Diego, CA: Prompt Scientific Publishing.

Proulx, C., & Lubell, W. D. (2011, June 5). Synthesis of substituted imidazolinones via a cationic gold(I)-mediated intramolecular cyclization. Poster presented at the Canadian Society for Chemistry, Montreal, Quebec.

Proulx, C., & Lubell, W. D. (2011, June 5). Teaching haemoglobin to third graders. Poster presented at the Canadian Society for Chemistry (CSC), Montreal, Quebec.

Proulx, C., & Lubell, W. D. (2011, June 5). Tuning the selectivity of GHRP-6 towards the CD36 vs GHS-R1a receptor by exploiting the reactivity of semicarbazones and aza-propargyl glycine in combinatorial azapeptide synthesis. Presented at the 94th Canadian Society of Chemistry Conference, Montréal, Québec.

Proulx, C., & Lubell, W. D. (2010). Aza-1,2,3-triazole-3-alanine Synthesis via Copper-Catalyzed 1,3-Dipolar Cycloaddition on Aza-progargylglycine. The Journal of Organic Chemistry, 75(15), 5385–5387. https://doi.org/10.1021/jo100957z

Proulx, C., & Lubell, W. D. (2010). Copper-Catalyzed N-Arylation of Semicarbazones for the Synthesis of Aza-Arylglycine-Containing Aza-Peptides. Organic Letters, 12(13), 2916–2919. https://doi.org/10.1021/ol100932m

Proulx, C., & Lubell, W. D. (2010, May 29). Copper-catalyzed N-arylation of a semicarbazone building block for the parallel synthesis of aryl-azaglycine containing azapeptides. Presented at the Canadian Society for Chemistry (CSC) meeting, Toronto, Ontario.

Proulx, C., & Lubell, W. D. (2010, March 21). Copper-catalyzed N-arylation of semicarbazones for the synthesis of aza-arylglycine containing aza-peptides. Poster presented at the American Chemical Society (ACS) meeting, San Francisco, California.

Bourguet, C. B., Proulx, C., Klocek, S., Sabatino, D., & Lubell, W. D. (2010). Solution-phase submonomer diversification of aza-dipeptide building blocks and their application in aza-peptide and aza-DKP synthesis. Journal of Peptide Science, 16(6), 284–296. https://doi.org/10.1002/psc.1235

Proulx, C., Boeglin, D., Chemtob, S., Ong, H., & Lubell, W. D. (2009, June 7). Aza-peptide analogs of GHRP-6 with selective receptor affinity for CD36 versus GHS-R1a.” Poster presented at the American Peptide Symposium (APS) meeting, Bloomington, Indiana.

Proulx, C., & Lubell, W. D. (2009, October 30). Cu(I)-catalyzed N-arylation of semicarbazones for the synthesis of aryl-aza glycine containing azapeptides. Poster presented at the Ontario Minisymposium in Synthetic and Bioorganic Chemistry (QOMSBOC) meeting, Québec.

Sabatino, D., Proulx, C., Klocek, S., Bourguet, C. B., Boeglin, D., Ong, H., & Lubell, W. D. (2009). Exploring Side-Chain Diversity by Submonomer Solid-Phase Aza-Peptide Synthesis. Organic Letters, 11(16), 3650–3653. https://doi.org/10.1021/ol901423c

Proulx, C., & Lubell, W. D. (2009). O-(3,4-Dihydro-4-oxo-1,2,3-benzotriazin-3-yl)-N,N,N’,N’-tetramethyluronium tetrafluoroborate. In L. A. Paquette (Ed.), Encyclopedia of Reagents for Organic Synthesis (2nd ed.). Hoboken, N.J.: John Wiley & Sons Ltd.

Proulx, C., & Lubell, W. D. (2009). O-(6-Chloro-1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate. In L. A. Paquette (Ed.), Encyclopedia of Reagents for Organic Synthesis (2nd ed.). Chichester: John Wiley & Sons Ltd.

Proulx, C., & Lubell, W. D. (2009). Solid-Phase Synthesis of Aza-Proline Analogs of GHRP-6. In M. Lebl (Ed.), Peptides: Breaking Away. Proceedings of the 21st American Peptide Symposium (pp. 56–57). San Diego, CA: Prompt Scientific Publishing.

Proulx, C., Boeglin, D., Chemtob, S., Ong, H., & Lubell, W. D. (2008, August 17). Aza-peptide analogs of GHRP-6 with selective receptor affinity for CD36 versus GHS-R1a.” Poster presented at the American Chemical Society (ACS) meeting, Philadelphia, Pennsylvania.

Ong, H., Chemtob, S., Lubell, W. D., Boeglin, D., Proulx, C., Sabatino, D., & Sajjadi, Z. (2008). Azapeptides as CD36 Binding Compounds (Patent No. PCT/CA2008/001162).

Proulx, C., Boeglin, D., Chemtob, S., Ong, H., & Lubell, W. D. (2008, November). Elucidation of structural and conformational requirements for GHRP-6 binding to the GHSR-1a and CD36 receptors using aza-peptides. Poster presented at the Québec-Ontario Minisymposium on Bio-Organic and Synthetic Chemistry (QOMSBOC) meeting, Toronto, Ontario.