Works (66)

Updated: April 4th, 2024 15:49

2024 journal article

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.

By: A. Galiakhmetov n, A. Shah n, A. Lane n, C. Davern n, C. Proulx n & A. Nevzorov n

author keywords: Solid-state NMR; Magnetically aligned bilayers; Lipids; Peptoids; Membrane proteins; Spectroscopic resolution
Sources: Web Of Science, NC State University Libraries
Added: January 16, 2024

2023 article

Late-Stage Chloride Displacements Enable Access to Peptoids with cis-Inducing Alkylammonium Side Chains

Davern, C. M., & Proulx, C. (2023, August 14). ORGANIC LETTERS, Vol. 8.

By: C. Davern n & C. Proulx n

UN Sustainable Development Goal Categories
Sources: Web Of Science, NC State University Libraries
Added: August 28, 2023

2022 journal article

Aligned peptoid-based macrodiscs for structural studies of membrane proteins by oriented-sample NMR

BIOPHYSICAL JOURNAL, 121(17), 3263–3270.

By: A. Galiakhmetov n, C. Davern n, R. Esteves n, E. Awosanya n, Q. Guthrie n, C. Proulx n, A. Nevzorov

MeSH headings : Glycine; Lipids; Magnetic Resonance Spectroscopy; Membrane Proteins / chemistry; Peptoids / chemistry
TL;DR: The NMR spectra measured for the membrane-bound form of Pf1 coat protein incorporated in this new lipid mimetics demonstrate a higher order parameter and uniform linewidths as compared to the conventional bicelles and peptide-based macrodiscs. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, NC State University Libraries
Added: October 11, 2022

2022 journal article

Late-Stage N-Alkylation of Azapeptides

ORGANIC LETTERS, 24(9), 1768–1773.

By: M. Bowles n & C. Proulx n

MeSH headings : Alkylation; Amino Acids; Aza Compounds / chemistry; Nitrogen; Tandem Mass Spectrometry
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Sources: Web Of Science, NC State University Libraries
Added: April 4, 2022

2022 article

On-resin C alpha-functionalization of N-arylglycinyl peptides with boronic acids

Young, H. A., & Proulx, C. (2022, May 19). ORGANIC & BIOMOLECULAR CHEMISTRY, Vol. 5.

By: H. Young n & C. Proulx n

MeSH headings : Boronic Acids / chemistry; Catalysis; Peptides / chemistry
TL;DR: A late-stage α-C-H functionalization reaction of resin-bound, electron-rich N-aryl peptides with boronic acid nucleophiles under mild conditions is reported. (via Semantic Scholar)
Sources: Web Of Science, NC State University Libraries
Added: June 13, 2022

2021 article

Solid phase submonomer azapeptide synthesis

SYNTHETIC AND ENZYMATIC MODIFICATIONS OF THE PEPTIDE BACKBONE, Vol. 656, pp. 169–190.

By: M. Bowles n & C. Proulx n

MeSH headings : Amino Acids; Aza Compounds; Peptides; Peptidomimetics; Solid-Phase Synthesis Techniques
TL;DR: This chapter provides a step-by-step protocol for the solid phase submonomer synthesis of azapeptides and focuses on semicarbazone functionalization by N-alkylation with primary alkyl halides, and describes conditions for coupling onto aza-amino acids. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, NC State University Libraries
Added: November 23, 2021

2021 article

Submonomer synthesis of peptoids containing trans-inducing N-imino- and N-alkylamino-glycines

Davern, C. M., Lowe, B. D., Rosfi, A., Ison, E. A., & Proulx, C. (2021, May 10). CHEMICAL SCIENCE, Vol. 5.

By: C. Davern n, B. Lowe n, A. Rosfi n, E. Ison n & C. Proulx n

TL;DR: The use of hydrazones as a new type of submonomer in peptoid synthesis is described, giving access to peptoid monomers that are structure-inducing and favors the trans-amide bond geometry by NMR, X-ray crystallography, and computational analyses. (via Semantic Scholar)
Sources: Web Of Science, NC State University Libraries
Added: June 10, 2021

2020 journal article

Atheroprotective and atheroregressive potential of azapeptide derivatives of GHRP-6 as selective CD36 ligands in apolipoprotein E-deficient mice

ATHEROSCLEROSIS, 307, 52–62.

By: G. Fregeau*, R. Sarduy*, H. Elimam*, C. Esposito*, K. Mellal*, L. Menard*, S. Graca*, C. Proulx* ...

author keywords: CD36; Azapeptides; Atherosclerosis; Macrophages; Regression
MeSH headings : Animals; Apolipoproteins E / genetics; Apolipoproteins E / metabolism; Atherosclerosis / drug therapy; Atherosclerosis / genetics; Atherosclerosis / prevention & control; CD36 Antigens; Disease Models, Animal; Ligands; Male; Mice; Mice, Inbred C57BL; Mice, Knockout; Oligopeptides / pharmacology
TL;DR: Development of CD36-selective azapeptide ligands merits consideration for treating atherosclerotic disease. (via Semantic Scholar)
Sources: Web Of Science, NC State University Libraries
Added: September 28, 2020

2020 article

Catching up to nature's ribosomes

Proulx, C. (2020, May 29). SCIENCE, Vol. 368, pp. 941–941.

By: C. Proulx n

MeSH headings : Proteins; Ribosomes
TL;DR: Hartrampf et al. (5) chemically synthesized single-domain proteins in hours by carefully optimizing iterative amino acid couplings on a solid support using a flow-chemistry setup. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, NC State University Libraries
Added: June 22, 2020

2020 journal article

N-Arylation of Amino Acid Esters to Expand Side Chain Diversity in Ketoxime Peptide Ligations

JOURNAL OF ORGANIC CHEMISTRY, 85(3), 1748–1755.

By: H. Young n, Q. Guthrie n & C. Proulx n

TL;DR: Palladium-catalyzed N-arylations of amino acid tert-butyl esters using 4-bromo-N,N-dimethylaniline as a coupling partner are reported, increasing the scope of Cα-substitution in ketoxime peptides. (via Semantic Scholar)
Sources: Web Of Science, NC State University Libraries
Added: March 16, 2020

2020 review

Peptide science: A "rule model" for new generations of peptidomimetics

[Review of ]. ACTA BIOMATERIALIA, 102, 35–74.

By: H. Reese n, C. Shanahan n, C. Proulx n & S. Menegatti n

author keywords: Peptides; Peptoids; Simulation; Peptidomimetics; Biomaterials
MeSH headings : Amino Acid Sequence; Molecular Dynamics Simulation; Peptidomimetics / chemistry; Peptoids / chemistry; Protein Structure, Secondary; Protein Structure, Tertiary; Sequence Analysis, Protein
TL;DR: Techniques to determine primary, secondary, and tertiary structure of peptides, and how they have been adapted to investigate peptoid structure are examined. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, NC State University Libraries
Added: February 27, 2020

2020 review

Synthesis and Biomedical Potential of Azapeptide Modulators of the Cluster of Differentiation 36 Receptor (CD36)

[Review of ]. BIOMEDICINES, 8(8).

By: C. Proulx n, J. Zhang*, D. Sabatino*, S. Chemtob*, H. Ong* & W. Lubell*

author keywords: semicarbazide; CD36; age-related macular degeneration; atherosclerosis; macrophage-driven inflammation; peptide
TL;DR: The translation of GHRP-6 to potent and selective linear and cyclic azapeptide modulators of CD36 is outlined in this review which highlights the relevance of turn geometry for activity and the biomedical potential of prototypes for the beneficial treatment of a wide range of cardiovascular, metabolic and immunological disorders. (via Semantic Scholar)
Sources: Web Of Science, NC State University Libraries
Added: November 2, 2020

2019 speech

Aerobic oxidation of N-aryl peptides for catalyst-free oxime ligations

Proulx, C. (2019, November). Presented at the Appalachian State University, Boone, NC.

By: C. Proulx

Event: Appalachian State University at Boone, NC on November 1, 2019

Source: NC State University Libraries
Added: March 4, 2021

2019 conference paper

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.

By: Q. Guthrie & C. Proulx

Event: American Chemical Society (ACS) meeting at Orlando, Florida on March 31 - April 4, 2019

Source: NC State University Libraries
Added: March 8, 2021

2019 journal article

Aza-Amino Acids Disrupt -Sheet Secondary Structures

MOLECULES, 24(10).

By: M. McMechen n, E. Willis n, P. Gourville n & C. Proulx n

author keywords: peptidomimetics; azapeptides; aza-amino acids; -hairpin; -sheet
MeSH headings : Amino Acid Sequence; Amino Acids / chemistry; Aza Compounds / chemistry; Aza Compounds / pharmacology; Hydrogen Bonding; Molecular Structure; Peptides / chemical synthesis; Peptides / chemistry; Protein Folding; Protein Structure, Secondary / drug effects; Proteins / chemistry; Solid-Phase Synthesis Techniques
TL;DR: The effect of a single aza-amino acid incorporation located in the upper β-strand at a hydrogen-bonded (HB) site of a β-hairpin model peptide (H-Arg-Tyr-Val-Glu- Val-d-Pro-Gly-Orn-Lys-Ile-Leu-Gln-NH2) is reported. (via Semantic Scholar)
Sources: Web Of Science, ORCID, NC State University Libraries
Added: July 1, 2019

2019 conference paper

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.

By: C. Proulx

Event: American Peptide Symposium at Monterey, CA on June 22-27, 2019

Source: NC State University Libraries
Added: March 8, 2021

2019 journal article

Ketoxime peptide ligations: oxidative couplings of alkoxyamines to N-aryl peptides

CHEMICAL SCIENCE, 10(41), 9506–9512.

By: Q. Guthrie n, H. Young n & C. Proulx n

TL;DR: Ketoxime peptides are readily accessible from oxidative couplings between N-aryl peptides and alkoxyamines under catalyst-free conditions. (via Semantic Scholar)
Sources: Web Of Science, NC State University Libraries
Added: November 18, 2019

2019 conference paper

New strategies for Ketoxime peptide ligations

Boulder Peptide Symposium 2019. Presented at the Boulder Peptide Symposium 2019, Boulder, CO.

By: C. Proulx

Event: Boulder Peptide Symposium 2019 at Boulder, CO on September 23-26, 2019

Source: NC State University Libraries
Added: March 4, 2021

2019 speech

Oxime ligation via in situ oxidation of N-phenylglycinyl peptides

Proulx, C. (2019, April). Presented at the Seton Hall University, South Orange, NJ.

By: C. Proulx

Event: Seton Hall University at South Orange, NJ on April 9, 2019

Source: NC State University Libraries
Added: March 4, 2021

2018 journal article

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.

By: D. Huynh*, V. Bessi*, L. Menard*, J. Piquereau*, C. Proulx n, M. Febbraio*, W. Lubell, A. Carpentier* ...

author keywords: ischemia/reperfusion; reactive oxygen species; PPAR-gamma; Langendorff; hemodynamics
MeSH headings : Adiponectin / biosynthesis; Animals; CD36 Antigens / agonists; Cardiotonic Agents / pharmacology; Disease Models, Animal; Gene Expression Regulation / drug effects; Mice; Mice, Knockout; Myocardial Reperfusion Injury / drug therapy; Myocardial Reperfusion Injury / metabolism; Myocardial Reperfusion Injury / pathology; Myocardium / metabolism; Myocardium / pathology; Oxidative Stress / drug effects; Peptides / pharmacology
TL;DR: 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 and may contribute to reduced reactive oxygen species generation and apoptosis after MI/R, in a CD36‐dependent manner. (via Semantic Scholar)
Sources: Web Of Science, NC State University Libraries
Added: August 6, 2018

2018 journal article

Glycosylated Peptoid Nanosheets as a Multivalent Scaffold for Protein Recognition

ACS Nano, 12(3), 2455–2465.

author keywords: protein-mimetic materials; molecular recognition; multivalent binding; two-dimensional nanomaterials; bioinspired polymers; cell-surface mimetics
MeSH headings : Binding Sites; Biomimetics; Biosensing Techniques; Concanavalin A / analysis; Concanavalin A / metabolism; Fluorescence Resonance Energy Transfer; Glycosylation; Hydrophobic and Hydrophilic Interactions; Lectins / analysis; Lectins / metabolism; Microscopy, Fluorescence; Models, Molecular; Monosaccharides / chemistry; Monosaccharides / metabolism; Nanostructures / chemistry; Nanostructures / ultrastructure; Peptoids / chemistry; Peptoids / metabolism; Protein Binding; Shiga Toxin / analysis; Shiga Toxin / metabolism; Trisaccharides / chemistry; Trisaccharides / metabolism; Wheat Germ Agglutinins / analysis; Wheat Germ Agglutinins / metabolism
TL;DR: An approach to mimic the cell surface presentation of carbohydrate ligands by the multivalent display of sugars on the surface of peptoid nanosheets, which may find utility in the inactivation of pathogens or as selective molecular recognition elements. (via Semantic Scholar)
UN Sustainable Development Goal Categories
7. Affordable and Clean Energy (OpenAlex)
Sources: Crossref, NC State University Libraries
Added: February 24, 2020

2018 journal article

Oxime Ligation via in situ Oxidation of N-Phenylglycinyl Peptides

ORGANIC LETTERS, 20(9), 2564–2567.

By: Q. Guthrie n & C. Proulx n

MeSH headings : Molecular Structure; Oxidation-Reduction; Oximes / chemistry; Peptides
TL;DR: Mild conditions for oxime ligations via in situ generation of α-imino amide intermediates, which can be fine-tuned by the electronic properties of the N-phenylglycine residue, offer unique advantages over conventional approaches for oximes ligations. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Sources: Web Of Science, NC State University Libraries
Added: August 6, 2018

2018 conference paper

Oxime ligation via in situ oxidation of N-phenylglycinyl peptides

Guthrie, Q. A., & Proulx, C. (2018, February 11). Presented at the Chemistry and Biology of Peptides Gordon Research Conference (GRC), Ventura, California.

By: Q. Guthrie & C. Proulx

Event: Chemistry and Biology of Peptides Gordon Research Conference (GRC) at Ventura, California on February 11-16, 2018

Source: NC State University Libraries
Added: March 4, 2021

2017 review

Azapeptide Synthesis Methods for Expanding Side-Chain Diversity for Biomedical Applications

[Review of ]. ACCOUNTS OF CHEMICAL RESEARCH, 50(7), 1541–1556.

By: R. Chingle*, C. Proulx* & W. Lubell*

MeSH headings : Amino Acids / chemistry; Aza Compounds / chemistry; Cyclization; Peptides / chemical synthesis; Peptides / chemistry
TL;DR: A remarkable stride to overcome this bottleneck was made in 2009 through the introduction of the submonomer procedure for azapeptide synthesis, which enabled addition of diverse side chains onto a common semicarbazone intermediate, providing a means to construct azapePTide libraries by solution- and solid-phase chemistry. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, NC State University Libraries
Added: August 6, 2018

2016 journal article

Design, Synthesis, Assembly, and Engineering of Peptoid Nanosheets

Accounts of Chemical Research, 49(3), 379–389.

By: E. Robertson*, A. Battigelli*, C. Proulx*, R. Mannige*, T. Haxton*, L. Yun*, S. Whitelam*, R. Zuckermann*

MeSH headings : Hydrophobic and Hydrophilic Interactions; Microscopy, Atomic Force; Microscopy, Electron; Microscopy, Fluorescence; Nanostructures; Peptoids / chemistry; Protein Engineering; X-Ray Diffraction
TL;DR: It is discovered that individual peptoid polymers with a simple sequence of alternating hydrophobic and ionic monomers can self-assemble into highly ordered, free-floating nanosheets, which provide a robust platform for the discovery of new classes of nanOSheets with tunable properties and novel applications. (via Semantic Scholar)
Sources: Crossref, NC State University Libraries
Added: February 24, 2020

2016 journal article

Improved chemical and mechanical stability of peptoid nanosheets by photo-crosslinking the hydrophobic core

Chemical Communications, 52(26), 4753–4756.

MeSH headings : Cross-Linking Reagents / chemistry; Electrophoresis, Polyacrylamide Gel; Hydrophobic and Hydrophilic Interactions; Microscopy, Fluorescence; Nanostructures / chemistry; Peptoids / chemistry; Photochemical Processes; Spectrum Analysis, Raman; Stress, Mechanical; X-Ray Diffraction
TL;DR: Photolabile monomers were introduced in order to crosslink the nanosheet interior to produce a more robust material that can survive sonication, lyophilization, and other biochemical manipulations. (via Semantic Scholar)
Sources: Crossref, NC State University Libraries
Added: February 24, 2020

2016 journal article

Molecular Engineering of the Peptoid Nanosheet Hydrophobic Core

Langmuir, 32(45), 11946–11957.

By: E. Robertson*, C. Proulx*, J. Su*, R. Garcia*, S. Yoo*, E. Nehls*, M. Connolly*, L. Taravati*, R. Zuckermann*

TL;DR: It is demonstrated that substitution at the meta and para positions of the Npe aromatic ring are well tolerated, enabling significant opportunities to tune the functional properties of peptoid nanosheets. (via Semantic Scholar)
Sources: Crossref, NC State University Libraries
Added: February 24, 2020

2016 journal article

On-resin N -terminal peptoid degradation: Toward mild sequencing conditions

Biopolymers, 106(5), 726–736.

By: C. Proulx*, F. Noë*, S. Yoo*, M. Connolly* & R. Zuckermann*

author keywords: peptoid sequencing; Edman degradation; N-terminal degradation
MeSH headings : Peptoids / chemistry; Peptoids / genetics; Proteolysis; Sequence Analysis, Protein / methods
TL;DR: It is demonstrated that sequential N‐terminal degradation of the first two residues proceeds in 87% and 74% conversions on average, respectively, and represents substantial progress toward a mild, iterative sequencing method for peptoid oligomers. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Sources: Crossref, NC State University Libraries
Added: August 28, 2020

2015 journal article

Accelerated Submonomer Solid-Phase Synthesis of Peptoids Incorporating Multiple Substituted N-Aryl Glycine Monomers

The Journal of Organic Chemistry, 80(21), 10490–10497.

MeSH headings : Glycine / analogs & derivatives; Glycine / chemistry; Macromolecular Substances / chemistry; Models, Molecular; Peptoids / chemical synthesis; Peptoids / chemistry; Solid-Phase Synthesis Techniques / methods
TL;DR: A straightforward enhancement to the submonomer method enables the rapid room temperature synthesis of a wide variety of N-aryl glycine-rich peptoid oligomers, possessing both electron-withdrawing and -donating substituents, in good yields. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Sources: Crossref, NC State University Libraries
Added: August 28, 2020

2015 conference paper

Molecular Engineering of the Peptoid Nanosheet Hydrophobic Core

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

By: C. Proulx, S. Yoo, M. Connolly & R. Zuckermann

Event: Canadian Society for Chemistry (CSC) meeting at Ottawa, Ontario on June 13-17, 2015

Source: NC State University Libraries
Added: September 23, 2021

2015 journal article

Peptoid nanosheets exhibit a new secondary-structure motif

Nature, 526(7573), 415–420.

By: R. Mannige*, T. Haxton*, C. Proulx*, E. Robertson*, A. Battigelli*, G. Butterfoss*, R. Zuckermann*, S. Whitelam*

MeSH headings : Amino Acid Motifs; Biomimetic Materials / chemical synthesis; Biomimetic Materials / chemistry; Models, Molecular; Molecular Dynamics Simulation; Nanostructures / chemistry; Peptoids / chemical synthesis; Peptoids / chemistry; Polymers / chemical synthesis; Polymers / chemistry; Porosity; Protein Structure, Secondary; Rotation; Water
TL;DR: The authors' simulations show that nanosheets are structurally and dynamically heterogeneous, can be formed only from peptoids of certain lengths, and are potentially porous to water and ions, and the concept of building regular structures from multiple rotational states can be generalized beyond the peptoid nanosheet system. (via Semantic Scholar)
Sources: Crossref, NC State University Libraries
Added: February 24, 2020

2014 journal article

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.

By: C. Proulx* & W. Lubell*

author keywords: peptide mimicry; imidazolin-2-ones; beta turns; gamma turns
MeSH headings : Amino Acids / chemistry; Crystallography, X-Ray; Imidazoles / chemical synthesis; Imidazoles / chemistry; Models, Molecular; Peptides / chemical synthesis; Peptides / chemistry; Protein Structure, Secondary; Thermodynamics
TL;DR: Conformational analysis in the solid state has provided insight to guide application of N‐amino‐imidazolin‐2‐ones in peptide mimicry and causes substantial effects on the ψi + 2 main chain and C‐terminal Phe χ1 side‐chain dihedral angles. (via Semantic Scholar)
Sources: Crossref, NC State University Libraries
Added: October 29, 2020

2014 journal article

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.

By: E. Robertson*, G. Olivier*, M. Qian*, C. Proulx*, R. Zuckermann* & G. Richmond*

author keywords: peptoid assembly; vibrational sum frequency spectroscopy; liquid surfaces; biomimetic polymers; protein mimetic materials
MeSH headings : Models, Molecular; Nanoparticles / chemistry; Oils / chemistry; Peptoids / chemistry; Pressure; Spectrum Analysis; Vibration; Water / chemistry
TL;DR: It is demonstrated that nanosheets can be formed via adsorption of peptoids at an oil–water interface using vibrational sum frequency spectroscopy and electrostatic interactions are essential in the formation of an ordered peptoid monolayer at the interface, a critical intermediate in the nanosheet assembly pathway. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Sources: Crossref, NC State University Libraries
Added: August 28, 2020

2014 conference paper

Improvements in the Solid-Phase Synthesis of Peptoids Incorporating Weak Nucleophile Submonomers

Proulx, C., Yoo, S., & Zuckermann, R. N. (2014, June 1). Presented at the Canadian Society for Chemistry (CSC) meeting, Vancouver, British Columbia.

By: C. Proulx, S. Yoo & R. Zuckermann

Event: Canadian Society for Chemistry (CSC) meeting at Vancouver, British Columbia on June 1-5, 2014

Source: NC State University Libraries
Added: February 5, 2022

2014 conference paper

Influence of Backbone Flexibility on the Two-dimensional Assembly of Peptoid Nanosheets

Proulx, C., Yoo, S., Connolly, M. D., & Zuckermann, R. N. (2014, August 10). Presented at the American Chemical Society (ACS) meeting, San Francisco, California.

By: C. Proulx, S. Yoo, M. Connolly & R. Zuckermann

Event: American Chemical Society (ACS) meeting at San Francisco, California on August 10-14, 2014

Source: NC State University Libraries
Added: February 5, 2022

2014 conference paper

Molecular Engineering of the Peptoid Nanosheet Hydrophobic Core

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

By: C. Proulx, J. Su, S. Yoo, G. Olivier, R. Garcia, M. Connolly, R. Mannige, T. Haxton, S. Whitelam, R. Zuckermann

Event: Annual User Meeting at Berkeley, California on August 25-26, 2014

Source: NC State University Libraries
Added: March 6, 2022

2014 conference paper

Multi-component Diversity-Oriented Synthesis of Aza-lysine-peptide Mimics

Zhang, J., Proulx, C., & Lubell, W. D. (2014, June 1). Presented at the Canadian Society for Chemistry (CSC) meeting, Vancouver, British Columbia.

By: J. Zhang, C. Proulx & W. Lubell

Event: Canadian Society for Chemistry (CSC) meeting at Vancouver, British Columbia on June 1-5, 2014

Source: NC State University Libraries
Added: February 5, 2022

2014 journal article

Multicomponent Diversity-Oriented Synthesis of Aza-Lysine-Peptide Mimics

Organic Letters, 16(1), 298–301.

By: J. Zhang*, C. Proulx*, A. Tomberg* & W. Lubell*

MeSH headings : Aza Compounds / chemical synthesis; Aza Compounds / chemistry; Lysine / analogs & derivatives; Lysine / chemical synthesis; Lysine / chemistry; Molecular Structure; Peptides / chemical synthesis; Peptides / chemistry
TL;DR: This effective method for making constrained aza-Lys-peptides offers strong potential for exploring various recognition events implicating lysine residues including post-translational peptide modification. (via Semantic Scholar)
Sources: Crossref, NC State University Libraries
Added: October 29, 2020

2014 chapter

Precision Sequence Control in Bioinspired Peptoid Polymers

In ACS Symposium Series (pp. 35–53).

By: J. Sun*, C. Proulx* & R. Zuckermann*

Sources: Crossref, NC State University Libraries
Added: June 24, 2021

2014 journal article

Structure-Determining Step in the Hierarchical Assembly of Peptoid Nanosheets

ACS Nano, 8(11), 11674–11684.

By: B. Sanii*, T. Haxton*, G. Olivier*, A. Cho*, B. Barton*, C. Proulx*, S. Whitelam*, R. Zuckermann*

author keywords: two-dimensional materials; supramolecular assembly; protein-mimetic materials; coarse-grained modeling; bioinspired polymers; interfacial assembly; monolayer compression
MeSH headings : Catalysis; Models, Molecular; Nanostructures; Peptoids / chemistry; Protein Conformation; Scattering, Radiation
TL;DR: The results provide a guide for using fluid interfaces to catalytically assemble 2D nanomaterials and find that lateral packing and organization of the chains occurs during the formation of a peptoid monolayer, prior to its collapse into a bilayer. (via Semantic Scholar)
Sources: Crossref, NC State University Libraries
Added: August 28, 2020

2012 journal article

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.

By: C. Proulx*, É. Picard*, D. Boeglin*, P. Pohankova*, S. Chemtob*, H. Ong*, W. Lubell*

MeSH headings : Amino Acid Sequence; Angiogenesis Inhibitors / chemistry; Angiogenesis Inhibitors / metabolism; Animals; Aza Compounds / chemistry; CD36 Antigens / metabolism; Cell Line; Inhibitory Concentration 50; Ligands; Oligopeptides / chemistry; Oligopeptides / metabolism; Protein Binding; Rats; Receptors, Ghrelin / metabolism
TL;DR: The synthetic hexapeptide growth hormone releasing peptide-6 (GHRP-6) exhibits dual affinity for the growth hormone secretagogue receptor 1a (GHS-R1a) and the cluster of differentiation 36 (CD36) receptor. (via Semantic Scholar)
Sources: Crossref, NC State University Libraries
Added: October 29, 2020

2012 journal article

N-Amino-imidazolin-2-one Peptide Mimic Synthesis and Conformational Analysis

Organic Letters, 14(17), 4552–4555.

By: C. Proulx* & W. Lubell*

MeSH headings : Combinatorial Chemistry Techniques; Crystallography, X-Ray; Cyclization; Imidazoles / chemical synthesis; Imidazoles / chemistry; Molecular Structure; Peptides / chemistry; Protein Conformation; Protein Structure, Secondary
TL;DR: Base-promoted 5-exo-dig cyclizations of aza-propargylglycinamides provided N-amino-imidazolin-2-one peptide mimics, which exhibited turn geometry in X-ray crystallographic and NMR spectroscopic analyses. (via Semantic Scholar)
Sources: Crossref, NC State University Libraries
Added: August 28, 2020

2012 report

Peptidomimetics Comprising N-Amino Cyclic Urea Residues and Uses Thereof

(Provisional Patent No. US 61/655,682).

By: W. Lubell, H. Ong, C. Proulx, R. Hopewell, K. Beauregard & Y. Garcia-Ramos

Source: NC State University Libraries
Added: March 6, 2022

2012 journal article

Synthesis of hydrazine and azapeptide derivatives by alkylation of carbazates and semicarbazones

Canadian Journal of Chemistry, 90(11), 985–993.

By: Y. Garcia-Ramos*, C. Proulx* & W. Lubell*

author keywords: carbazate; tetraethylammonium hydroxide; semicarbazone; alkylation; fluorenone hydrazine
Sources: Crossref, NC State University Libraries
Added: December 18, 2021

2011 journal article

Azapeptides and their therapeutic potential

Future Medicinal Chemistry, 3(9), 1139–1164.

By: C. Proulx*, D. Sabatino*, R. Hopewell*, J. Spiegel*, Y. García Ramos* & W. Lubell

MeSH headings : Aza Compounds / chemical synthesis; Aza Compounds / chemistry; Aza Compounds / pharmacology; Aza Compounds / therapeutic use; Enzyme Inhibitors / chemistry; Enzyme Inhibitors / pharmacology; Enzyme Inhibitors / therapeutic use; Humans; Molecular Conformation; Peptides / chemical synthesis; Peptides / chemistry; Peptides / pharmacology; Peptides / therapeutic use; Semicarbazides / chemical synthesis; Semicarbazides / chemistry; Semicarbazides / pharmacology; Semicarbazides / therapeutic use; Structure-Activity Relationship
TL;DR: This review aims to provide a historical look at the development of azapeptide science along with a focus on recent developments and perspectives on the future of this useful tool for medicinal chemistry. (via Semantic Scholar)
Sources: Crossref, NC State University Libraries
Added: December 16, 2021

2011 conference paper

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

Proulx, C., & Lubell, W. D. (2011, June 25). Poster presented at the American Peptide Symposium (APS), San Diego, California.

By: C. Proulx & W. Lubell

Event: American Peptide Symposium (APS) at San Diego, California on June 25-30, 2011

Source: NC State University Libraries
Added: March 6, 2022

2011 journal article

Modified peptide monolayer binding His-tagged biomolecules for small ligand screening with SPR biosensors

The Analyst, 136(15), 3142.

By: O. Bolduc*, P. Lambert-Lanteigne*, D. Colin*, S. Zhao*, C. Proulx*, D. Boeglin*, W. Lubell*, J. Pelletier* ...

MeSH headings : Adsorption; Amino Acid Sequence; Animals; CD36 Antigens / metabolism; Cattle; Drug Evaluation, Preclinical / methods; Histidine / chemistry; Histidine / metabolism; Humans; Immobilized Proteins / chemistry; Immobilized Proteins / metabolism; Ligands; Peptides / chemistry; Peptides / metabolism; Protein Binding; Small Molecule Libraries / pharmacology; Surface Plasmon Resonance / methods; Tetrahydrofolate Dehydrogenase / chemistry; Tetrahydrofolate Dehydrogenase / metabolism
TL;DR: Modification of this peptide monolayer with Nα,Nα-bis(carboxymethyl)-L-lysine gave a surface competent for binding His-tagged proteins, as demonstrated using enzyme (human dihydrofolate reductase), protein/antibody and receptor (CD36) examples. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Sources: Crossref, NC State University Libraries
Added: August 28, 2020

2011 journal article

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.

By: D. Sabatino*, C. Proulx*, P. Pohankova, H. Ong & W. Lubell

MeSH headings : Amino Acid Sequence; Animals; Aza Compounds / chemical synthesis; Aza Compounds / chemistry; Aza Compounds / pharmacology; CD36 Antigens / metabolism; Oligopeptides / chemical synthesis; Oligopeptides / chemistry; Oligopeptides / pharmacology; Protein Binding; Rats; Solid-Phase Synthesis Techniques; Spectrum Analysis; Structure-Activity Relationship
TL;DR: The potential of introducing salt bridges to furnish GHRP-6 azapeptide ligands of the CD36 receptor with relatively high affinity is explored, considering that aromatic cation interactions may contribute to binding affinity. (via Semantic Scholar)
Sources: Crossref, NC State University Libraries
Added: August 28, 2020

2011 conference paper

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.

By: C. Proulx & W. Lubell

Ed(s): M. Lebl

Event: 22nd American Peptide Symposium at Harbor Island, San Diego, CA on June 25-30, 2011

Source: NC State University Libraries
Added: March 6, 2022

2011 conference paper

Synthesis of substituted imidazolinones via a cationic gold(I)-mediated intramolecular cyclization

Proulx, C., & Lubell, W. D. (2011, June 5). Poster presented at the Canadian Society for Chemistry, Montreal, Quebec.

By: C. Proulx & W. Lubell

Event: Canadian Society for Chemistry at Montreal, Quebec on June 5-9, 2011

Source: NC State University Libraries
Added: June 25, 2022

2011 conference paper

Teaching haemoglobin to third graders

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

By: C. Proulx & W. Lubell

Event: Canadian Society for Chemistry (CSC) at Montreal, Quebec on June 5-9, 2011

Source: NC State University Libraries
Added: June 25, 2022

2011 conference paper

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

Proulx, C., & Lubell, W. D. (2011, June 5). Presented at the 94th Canadian Society of Chemistry Conference, Montréal, Québec.

By: C. Proulx & W. Lubell

Event: 94th Canadian Society of Chemistry Conference at Montréal, Québec on June 5-9, 2011

Source: NC State University Libraries
Added: March 6, 2022

2010 journal article

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.

By: C. Proulx* & W. Lubell*

MeSH headings : Alanine / analogs & derivatives; Alanine / chemical synthesis; Alkynes / chemistry; Aza Compounds / chemical synthesis; Aza Compounds / chemistry; Catalysis; Chromatography, High Pressure Liquid; Copper / chemistry; Cyclization; Glycine / analogs & derivatives; Glycine / chemistry; Mass Spectrometry
TL;DR: Circular dichroism spectroscopy in water demonstrated that azapeptides which possess an aza-1,2,3-triazole-3-alanine residue at the Trp(4) position of the GHRP-6 sequence adopt beta-turn conformations. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Sources: Crossref, NC State University Libraries
Added: August 28, 2020

2010 journal article

Copper-Catalyzed N-Arylation of Semicarbazones for the Synthesis of Aza-Arylglycine-Containing Aza-Peptides

Organic Letters, 12(13), 2916–2919.

By: C. Proulx* & W. Lubell*

MeSH headings : Aza Compounds / chemical synthesis; Aza Compounds / chemistry; Catalysis; Copper / chemistry; Glycine / analogs & derivatives; Glycine / chemistry; Iodides / chemistry; Molecular Conformation; Peptides / chemical synthesis; Peptides / chemistry; Semicarbazones / chemistry; Stereoisomerism
TL;DR: Parallel synthesis of 13 aza-arylglycine peptides, based on the hexapeptide sequence of Growth Hormone Releasing Peptide-6 (GHRP-6), was accomplished via selective N-arylation of a semicarbazone peptide building block anchored on Rink amide resin. (via Semantic Scholar)
Sources: Crossref, NC State University Libraries
Added: October 29, 2020

2010 conference paper

Copper-catalyzed N-arylation of a semicarbazone building block for the parallel synthesis of aryl-azaglycine containing azapeptides

Proulx, C., & Lubell, W. D. (2010, May 29). Presented at the Canadian Society for Chemistry (CSC) meeting, Toronto, Ontario.

By: C. Proulx & W. Lubell

Event: Canadian Society for Chemistry (CSC) meeting at Toronto, Ontario on May 29 - June 2, 2010

Source: NC State University Libraries
Added: June 25, 2022

2010 conference paper

Copper-catalyzed N-arylation of semicarbazones for the synthesis of aza-arylglycine containing aza-peptides

Proulx, C., & Lubell, W. D. (2010, March 21). Poster presented at the American Chemical Society (ACS) meeting, San Francisco, California.

By: C. Proulx & W. Lubell

Event: American Chemical Society (ACS) meeting at San Francisco, California on March 21-25, 2010

Source: NC State University Libraries
Added: June 25, 2022

2010 journal article

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.

By: C. Bourguet*, C. Proulx*, S. Klocek*, D. Sabatino* & W. Lubell*

author keywords: alkylation; aza-Gly-Xaa; aza-peptide; beta-turn conformation; benzophenone semicarbazone protecting group; DKP; aza-DKP; triazine
MeSH headings : Amino Acid Sequence; Benzophenones / chemistry; Carcinogens / chemistry; Dipeptides / chemical synthesis; Dipeptides / chemistry; Hydrazines / chemistry; Molecular Structure; Semicarbazones / chemistry
Sources: Crossref, NC State University Libraries
Added: August 28, 2020

2009 conference paper

Aza-peptide analogs of GHRP-6 with selective receptor affinity for CD36 versus GHS-R1a”

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.

By: C. Proulx, D. Boeglin, S. Chemtob, H. Ong & W. Lubell

Event: American Peptide Symposium (APS) meeting at Bloomington, Indiana on June 7-12, 2009

Source: NC State University Libraries
Added: June 25, 2022

2009 conference paper

Cu(I)-catalyzed N-arylation of semicarbazones for the synthesis of aryl-aza glycine containing azapeptides

Proulx, C., & Lubell, W. D. (2009, October 30). Poster presented at the Ontario Minisymposium in Synthetic and Bioorganic Chemistry (QOMSBOC) meeting, Québec.

By: C. Proulx & W. Lubell

Event: Ontario Minisymposium in Synthetic and Bioorganic Chemistry (QOMSBOC) meeting at Québec on October 30 - November 1, 2009

Source: NC State University Libraries
Added: June 25, 2022

2009 journal article

Exploring Side-Chain Diversity by Submonomer Solid-Phase Aza-Peptide Synthesis

Organic Letters, 11(16), 3650–3653.

By: D. Sabatino, C. Proulx*, S. Klocek, C. Bourguet, D. Boeglin, H. Ong, W. Lubell

MeSH headings : Amino Acid Sequence; Aza Compounds / chemical synthesis; Aza Compounds / chemistry; CD36 Antigens / metabolism; Catalysis; Circular Dichroism; Combinatorial Chemistry Techniques; Oligopeptides / chemical synthesis; Oligopeptides / chemistry; Stereoisomerism
TL;DR: Circular dichroism demonstrated that azaPhe-peptide 7a induced a beta-turn conformation which may be responsible for its 1000-fold improvement in GHRP-6 selectivity for the CD36 receptor. (via Semantic Scholar)
Sources: Crossref, NC State University Libraries
Added: August 28, 2020

2009 chapter

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.

By: C. Proulx & W. Lubell

Ed(s): L. Paquette

Source: NC State University Libraries
Added: March 6, 2022

2009 chapter

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.

By: C. Proulx & W. Lubell

Ed(s): L. Paquette

Source: NC State University Libraries
Added: March 6, 2022

2009 chapter

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.

By: C. Proulx & W. Lubell

Ed(s): M. Lebl

Event: 21st American Peptide Symposium

Source: NC State University Libraries
Added: June 25, 2022

2008 conference paper

Aza-peptide analogs of GHRP-6 with selective receptor affinity for CD36 versus GHS-R1a”

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.

By: C. Proulx, D. Boeglin, S. Chemtob, H. Ong & W. Lubell

Event: American Chemical Society (ACS) meeting at Philadelphia, Pennsylvania on August 17-21, 2008

Source: NC State University Libraries
Added: June 25, 2022

2008 report

Azapeptides as CD36 Binding Compounds

(Patent No. PCT/CA2008/001162).

By: H. Ong, S. Chemtob, W. Lubell, D. Boeglin, C. Proulx, D. Sabatino, Z. Sajjadi

Source: NC State University Libraries
Added: June 25, 2022

2008 conference paper

Elucidation of structural and conformational requirements for GHRP-6 binding to the GHSR-1a and CD36 receptors using aza-peptides

Proulx, C., Boeglin, D., Chemtob, S., Ong, H., & Lubell, W. D. (2008, November). Poster presented at the Québec-Ontario Minisymposium on Bio-Organic and Synthetic Chemistry (QOMSBOC) meeting, Toronto, Ontario.

By: C. Proulx, D. Boeglin, S. Chemtob, H. Ong & W. Lubell

Event: Québec-Ontario Minisymposium on Bio-Organic and Synthetic Chemistry (QOMSBOC) meeting at Toronto, Ontario

Source: NC State University Libraries
Added: June 25, 2022

Employment

Updated: January 23rd, 2023 17:40

2016 - present

North Carolina State University Raleigh, NC, US
Assistant Professor Department of Chemistry

2012 - 2016

Lawrence Berkeley National Laboratory CA, CA, US
Postdoctoral Fellow Molecular Foundry

Education

Updated: January 23rd, 2023 17:40

2007 - 2012

Université de Montréal Montreal, QC, CA
Ph.D Departement de Chimie

2003 - 2007

University of Ottawa Ottawa, ON, CA
B.Sc. Department of Chemistry

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