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Publications at NCSU

38. Galiakhmetov, A. R.; Shah, A. A.; Lane, A.; Davern, C. M.; Proulx, C.; Nevzorov, A. A.* Peptoid-based macrodiscs of variable lipid composition for structural studies of membrane proteins by oriented-sample solid-state NMR. Journal of Structural Biology: X 2024, 9, 100095.

37. Davern, C. M.; Proulx, C.* “Late-Stage Chloride Displacements Enable Access to Peptoids with cis-Inducing Alkylammonium Side Chains” Org. Lett. 2023, 25, 6195-6199.


36. Galiakhmetov, A. R.; Davern, C. M.; Esteves, R. J. A.; Awosanya, E. O.; Guthrie, Q. A. E.; Proulx, C.; Nevzorov, A. A.* “Aligned Peptoid-Based Macrodiscs for the Structural Studies of Membrane Proteins by Oriented-Sample NMR.” Biophysical Journal. 2022, 121, 3263-3270.

35. Young, H. A.; Proulx, C.* "On-Resin Cα-Functionalization of N-Arylglycinyl Peptides with Boronic Acids". Org. Biomol. Chem. 2022, 20, 6245 - 6249


34. Bowles, M. O.; Proulx, C.* "Late-Stage N-alkylation of Azapeptides". Org. Lett. 2022, 24, 1768-1773. 


33. Davern, C. M.; Lowe, B. D.; Rosfi, A.; Ison, E. A.; Proulx, C.* "Submonomer Synthesis of Peptoids Containing trans-inducing N-imino-
and N-alkylamino-glycine Monomers".
Chem. Sci. 2021, 12, 8401-8410.


32. Bowles, M.; Proulx, C.* "Solid Phase Submonomer Azapeptide Synthesis". In Methods in Enzymology, ed. E. J. Petersson, Academic Press: 2021, vol. 656, pp. 169-190. 

31. Proulx, C. "Catching up to nature's ribosomes". Science 2020, 368, 941.

*Perspective on an article by Hartrampf, N. et al. Synthesis of proteins by automated flow chemistry. Science 2020, 368, 980-987.

30. Young, H. A.; Guthrie, Q. A. E.; Proulx, C.* "N-Arylation of Amino Acid Esters to Expand Side Chain Diversity in Ketoxime Peptide Ligations". J. Org. Chem. 2020, 85, 1748-1755.

*Featured in a special issue on "Modern Peptide and Protein Chemistry".


29. Reese, H. R.; Shanahan, C. C.; Proulx, C.; Menegatti, S.* "Peptide science: a ”rule model” for new generations of peptidomimetics". Acta Biomaterialia 2020, 102, 35-74.

Menegatti TOC.jpg

28. Guthrie, Q. A. E; Young, H. A.; Proulx, C.* "Ketoxime peptide ligations: oxidative couplings of alkoxyamines to N-aryl peptides".Chem. Sci. 201910,  9506-9512.


27. McMechen, M. A.; Willis, E. L.; Gourville, P. C.; Proulx, C.* "Aza-amino acids disrupt beta-sheet secondary structures". Molecules 2019, 24, 1919.

*Featured in a special issue on  Advances in Peptide and Peptidomimetic Design Inspiring Basic Science and Drug Discovery: A Themed Issue Honoring Professor Victor J. Hruby on the Occasion of His 80th Birthday

TOC azapeptide.png

26. Guthrie, Q. A. E.; Proulx, C.* "Oxime Ligation via in situ Oxidation of N-Phenylglycinyl Peptides". Org. Lett. 2018, 20, 2564-2567.

*Highlighted in SYNFORM, published online: August 3rd, 2018.

At NCSU, from postdoctoral and Ph.D. work

25. Proulx, C.; Zhang, J.; Sabatino, D.; Chemtob, S.; Ong, H.; Lubell, W. D. Synthesis and Biomedical Potential of Azapeptide Modulators of the Cluster of Differentiation 36 Receptor (CD36). Biomedicines. 2020, 8, 241.

24. Frégeau, G.; Sarduy, R.; Elimam, H.; Esposito, C. L.; Mellal, K.; Ménard, L.; Leitão da Graça, S. D.; Proulx, C.; Zhang, J.; Febbraio, M.; Soto, Y.; Lubell, W. D.; Ong, H.; Marleau, S. Atheroprotective and atheroregressive potential of azapeptide derivatives of GHRP-6 as selective CD36 ligands in apolipoprotein E-deficient mice. Atherosclerosis 2020. 307, 52-62.

23. Battigelli, A.; Kim, J. H.; Dehigaspitiya, D. C.; Proulx, C.; Robertson, E. J.; Murray, D. J.; Rad, B.; Kirshenbaum, K.; Zuckermann, R. N. “Glycosylated Peptoid Nanosheets as a Multivalent Scaffold for Protein Recognition.” ACS Nano2018, 12, 2455-2465.

22. Huynh, D. N.; Bessi, V. L.; Menard, L.; Piquereau, J.; Proulx, C.; Febbraio, M.; Lubell, W. D.; Carpentier, A. C.; Burelle, Y.; Ong, H.; Marleau, S. "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 J. 2018, 32, 807-818.

21. Chingle, R.; Proulx, C.; Lubell, W. D.  “Azapeptide Synthesis Methods for Expanding Side-Chain Diversity for Biomedical Applications” Acc. Chem. Res. 201750, 1541-1556.

From postdoctoral and Ph.D. work

20. Robertson, E. J.; Proulx, C.; Su, J. K.; Garcia, R. L.; Yoo, S.; Nehls, E. M.; Connolly, M. D.; Taravati, L.; Zuckermann, R. N.  “Molecular Engineering of the Peptoid Nanosheet Hydrophobic Core” Langmuir 2016, 32, 11946-11957.

*Featured as the ACS Editors' Choice and the front cover for the November  15th, 2016 issue.

19. Proulx, C.; Noë, F.; Yoo, S.; Connolly, M. D.; Zuckermann, R. N. “On-Resin N-Terminal Peptoid Degradation: Toward Mild Sequencing Conditions” Biopolymers (Pept. Sci.) 2016, 106, 726-736.

18. Flood, D.; Proulx, C.; Robertson, E. J.; Battigelli, A.; Wang, S.; Schwartzberg, A.; Zuckermann, R. N. “Improved Chemical and Mechanical Stability of Peptoid Nanosheets by Photo-crosslinking the Hydrophobic Core” Chem. Commun. 2016, 52, 4753-4756.

*Featured as the inside front cover for the April 4th, 2016 issue.

17. Robertson, E. J.; Battigelli, A.; Proulx, C.; Mannige, R. V.; Haxton, T. K.; Whitelam, S.; Zuckermann, R. N. “Design, Synthesis, Assembly and Engineering of Peptoid Nanosheets”. Acc. Chem. Res. 2016,49, 379-389.

*Featured as the front cover for the March 16th, 2016 issue.

16. Mannige, R. V.; Haxton, T. K.; Proulx, C.; Robertson, E. J.; Battigelli, A.; Butterfoss, G. L.; Zuckermann, R. N.; Whitelam, S. “Peptoid Nanosheets Exhibit a New Secondary Structure Motif”. Nature 2015, 526, 415-420.

*Featured in a C&En news article: “Peptoids Do a Double Twist“, C&En, October 12th, 2015, 93(40), p.30.

15. Proulx, C.; Yoo, S.; Connolly. M. D.; Zuckermann, R. N. “Accelerated Submonomer Solid-Phase Synthesis of Peptoids Incorporating Multiple Substituted N-Aryl Glycine Monomers”. J. Org. Chem. 2015, 80, 10490-10497.

*Featured as the front cover for the November 6th, 2015 issue.

14. Sanii, B.; Haxton, T. K.; Olivier, G. K.; Cho, A.; Barton, B.; Proulx, C.; Whitelam, S.; Zuckermann, R. N. “Structure-Determining Step in the Hierarchical Assembly of Peptoid Nanosheets”. ACS Nano 2014, 8, 11674-11684.

13. Robertson, E. J.; Olivier, G. K.; Qian, M.; Proulx, C.; Zuckermann, R. N.; Richmond, G. L. “Assembly and Molecular Order of Two-Dimensional Peptoid Nanosheets at the Oil-Water Interface”. Proc. Natl. Acad. Sci. 2014, 111, 13284-13289.

12. Zhang, J.; Proulx, C.; Tomberg, A.; Lubell, W. D. “Multicomponent Diversity-Oriented Synthesis of Aza-Lysine-Peptide Mimics”. Org. Lett. 2014, 16, 298-301.

11. Proulx, C.; Lubell, W. D. “Analysis of N-amino-imidazolin-2-one Peptide Turn Mimic 4-position Substituent Effects on Conformation by X-ray Crystallography”. Biopolymers (Pept. Sci.) 2014, 102, 7-15.

10. Proulx, C.; Lubell, W. D. “N-Amino-imidazolin-2-one Peptide Mimic Synthesis and Conformational Analysis”. Org. Lett. 2012, 14, 4552-4555.

*Article recognized as a significant contribution in the field of peptide sciences by Dr. Roger Freidinger (F1000 Faculty).

9. García-Ramos, Y.; Proulx, C.; Lubell, W. D. “Synthesis of Hydrazine and Azapeptide Derivatives by Alkylation of Carbazates and Semicarbazones”. Can. J. Chem. 2012, 90, 985-993

8. Proulx, C.; Picard, É.; Boeglin, D.; Pohankova, P.; Chemtob, S.; Ong, H.; Lubell, W. D. “Azapeptide Analogs of the Growth Hormone Releasing Peptide 6 as Cluster of Differentiation 36 Receptor Ligands with Reduced Affinity for the Growth Hormone Secretagogue Receptor 1a”. J. Med. Chem. 2012, 55, 6502–6511.

7. Sabatino, D.; Proulx, C.; Pohankova, P.; Ong, H.; Lubell, W. D. “Structure-Activity Relationships of GHRP-6 Azapeptide Ligands of the CD36 Scavenger Receptor by Solid-Phase Submonomer Azapeptide Synthesis”. J. Am. Chem. Soc. 2011, 133, 12493-12506.

6. Proulx, C.; Sabatino, D.; Hopewell, R.; Spiegel, J.; García Ramos, Y.; Lubell, W. D. “Azapeptides and their Therapeutic Potential”. Future Med. Chem. 2011, 3, 1139–1164.

5. Bolduc, O. R.; Lambert-Lanteigne, P.; Colin, D. Y.; Zhao, S. S.; Proulx, C.; Boeglin, D.; Lubell, W. D.; Pelletier, J. N.; Féthière, J.; Ong, H.; Masson, J.-F. “Modified Peptide Monolayer Binding His-tagged Biomolecules for Small Ligand Screening with SPR Biosensors”. Analyst 2011, 136, 3142-3148.

4. Proulx, C.; Lubell, W. D. “Aza-1,2,3-triazole-3-alanine Synthesis via Copper-Catalyzed 1,3-Dipolar Cycloaddition on Aza-progargylglycine”. J. Org. Chem. 2010, 75, 5385-5387.

*Article in Synfacts (2010) 11: 1311.

3. Proulx, C.; Lubell, W. D. “Copper-Catalyzed N-Arylation of Semicarbazones for the Synthesis of Aryl-Azaglycine Containing Azapeptides”. Org. Lett. 2010, 12, 2916-2919.

2. Bourguet, C. B.; Proulx, C.; Klocek, S.; Sabatino, D.; Lubell, W. D. “Solution-phase Submonomer Diversification of Aza-dipeptide Building Blocks and their Application in Aza-peptide and Aza-DKP Synthesis”. J. Pept. Sci. 2010, 16, 284-296.

1. Sabatino, D.; Proulx, C.; Klocek, S.; Bourguet, C. B; Boeglin, D.; Ong, H.; Lubell, W. D. “Exploring Side-Chain Diversity by Submonomer Solid-Phase Aza-Peptide Synthesis”. Org. Lett. 2009, 11, 3650-3653.

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