Stockdill Group Publications

Independent Publications (*indicates corresponding author, ‡indicates equal authorship, undergraduate co-authors are underlined):

31) Morsy, R. M. I.;‡ Samala, G.; ‡ Jalan, A.; Kopach, M. E.; Stockdill, J. L.* Under revision.

30) Venneti, N. M.; Stockdill, J. L.* Stretching Peptides’ Potential to Target Protein-Protein Interactions. ACS Central Science 2023, DOI: 10.1021/acscentsci.3c00364.

29) Venneti, N. M.; Samala, G.;‡ Morsy, R. M. I.;‡ Mendoza, L. G.; Isidro-Llobet,A.; Tom, J. K.; Mukherjee, S.; Kopach, M. E.; Stockdill, J. L.* Phosphine-dependent photoinitiation of alkyl thiols under near-UV light facilitates user-friendly peptide desulfurization. J. Am. Chem. Soc. 2023, 145, 1053–1061.

28) Zastepa, A.;* Westrick, J. A.; Liang, A.; Birbeck, J. A.; Furr, E.; Watson, C. L.; Stockdill, J. L.; Ramakrishna, B. S.; Crevecoeur, S.; Broad screening of toxic and bioactive metabolites in cyanobacterial and harmful algal blooms in Lake of the Woods (Canada-USA), 2016-2019. J. Great Lakes Res. 2023, 49, 134–146.

27) Stockdill, J. L., Arbour, C. A., inventors. Wayne State University, assignee. Epimerization-free N to C solid-phase peptide synthesis. U.S. Patent 11,427,612, issued Aug 30, 2022.

26) Arbour, C. A.; Mendoza, L. G.; Stockdill, J.L.* Recent Advances in the Synthesis of C-Terminally Modified Peptides. Org. Biomol. Chem. 2020, 18, 7253– 7272.

25) Zhu, S.; Samala, G.; Sletten, E. T.; Stockdill, J. L.;* Nguyen, H. M.* Facile Triflic Acid-Catalyzed -1,2-cis-Thiol Glycosylations: Scope and Application to the Synthesis of S-Linked Oligosaccharides, Glycolipids, Sublancin Glycopeptide and TN/TF Antigens. Chem. Sci. 2019, 10,10475–10480. Featured as part of the Chemical Science 2019 HOT Article Collection and on the back cover of the Journal:

     

24) Arbour, C. A.; Belavek, K. J.; Tariq, R.; Mukherjee, S.; Tom, J. K.; Isidro-Llobet, A.; Kopach, M. E.; Stockdill, J. L.* Bringing Macrolactamization Full Circle: Self-Cleaving Head-to-Tail Macrocyclization of Unprotected Peptides via Mild N-Acyl Urea Activation J. Org. Chem. 2019, 84, 1035–1041. [Supporting Information]

23) Kondasinghe, T. D.; Saraha, H. Y.; Jackowski, S. T.; Stockdill, J. L.* Raising the Bar On-Bead: Efficient On-Resin Synthesis of alpha-Conotoxin LvIA. Tetrahedron Lett. 2019, 60, 23–28. [Supporting Information]

22) Sirinimal, H. S.;‡ Hebert, S. P.;‡ Samala, G.; Chen, H.; Rosenhauer, G. J.; Schlegel, H. B.;* Stockdill, J. L.* A Synthetic and Computational Study of Tin-Free Reductive Tandem Cyclizations of Neutral Aminyl Radicals. Org. Lett. 2018, 20, 6340–6344. DOI: 10.1021/acs.orglett.8b02456. [Supporting Information – Synthetic, Computational]

21) Arbour, C. A.; Stockdill, J. L.* A mild capping method for SPPS on the N-methyl diaminobenzoyl linker: synthesis of an N-acyl urea appended C. elegans neuropeptide. Tetrahedron Lett. 2018, 59, 3903–3906. [Supporting Information]

20) Lopez, A. M.;‡ Ibrahim, A. I.;‡ Rosenhauer, G. J.; Sirinimal, H. S.; Stockdill, J. L.* Tin-Free Access to the ABC Core of the Calyciphylline A Alkaloids and Unexpected Formation of a D-Ring-Contracted Tetracyclic Core. Org. Lett. 2018, 20, 2216–2219. [Supporting Information]

19) Arbour, C. A.;‡ Stamatin, R. E.;‡ Stockdill, J. L.* Sequence Diversification by Divergent C-Terminal Elongation of Peptides. J. Org. Chem. 2018, 83,1797–1803. [Supporting Information]

18) Arbour, C. A.; Kondasinghe, T. D.; Saraha, H. Y.; Vorlicek, T. L.; Stockdill, J. L.* Epimerization-Free Access to C-Terminal Cysteine Peptide Acids, Carboxamides, Secondary Amides, and Esters via Complimentary Strategies. Chem. Sci. 2018, 9, 350–355. [Supporting Information]

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17) Arbour, C. A.; Saraha, H. Y.; McMillan, T. F.; Stockdill, J. L. * Exploiting the MeDbz Linker to Generate Protected or Unprotected C-Terminally Modified Peptides. Chem. Eur. J. 2017, 23, 12484–12488. [Supporting Information]

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16) Kondasinghe, T. D.;‡ Saraha, H. Y.;‡ Odeesho, S. B.; Stockdill, J. L.* Direct Palladium-Mediated On-Resin Disulfide Formation from Allocam Protected Peptides. Org. Biomol. Chem. 2017, 15, 2914–2918. [Supporting Information] Selected for inclusion in the themed collection: ‘Celebrating excellence in research: women of organic chemistry.’ RSC Tweet here.

15) Fandrick, D. R.;* Hart, C. A.; Okafor, I. S.; Mercadante, M. A.; Sanyal, S.; Masters, J. T.; Sarvestani, M.; Fandrick, K. R.; Stockdill, J. L.; Grinberg, N.; Gonnella, N.; Lee, H.; Senanayake, C. H. Copper-Catalyzed Asymmetric Propargylation of Cyclic Aldimines Org. Lett. 2016, 18, 6192–6195. [Supporting Information]

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14) Yang, Y.Y.; Ibrahim, A. A.; Hashemi, P.;* Stockdill, J. L.* Real-Time, Selective Detection of Copper(II) using Ionophore-Grafted Carbon-Fiber Microelectrodes. Anal. Chem. 2016, 88, 6962–6966. [Supporting Information]TOC5 copy

13) Yang, Y.Y; Ibrahim, A. A.; Stockdill, J. L.;* Hashemi, P.* A Density-Controlled Scaffolding Strategy for Covalent Functionalization of Carbon-Fiber Microelectrodes. Anal. Methods 2015, 7, 7352–7357. Part of the 2015 Emerging Investigators Themed Collection [Supporting Information]

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12) Stockdill, J. L.;* Lopez, A. M.; Ibrahim, A. A. Toward the ABCD Core of the Calyciphylline A-Type Daphniphyllum Alkaloids: Solvent non-Innocence in Neutral Aminyl Radical Cyclizations. Tetrahedron Lett. 2015, 56, 3503–3506. Invited Submission to Symposium in Print in Memory of Harry Wasserman. [Supporting Information]

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11)  Ibrahim, A. A.; Golonka, A. N.; Lopez, A. M.; Stockdill, J. L.* Rapid Access to the Heterocyclic Core of the Calyciphylline A and Daphnicyclidin A-type Daphniphyllum Alkaloids via Tandem Cyclization of a Neutral Aminyl Radical. Org. Lett. 2014, 16, 1072–1075. Highlighted in Doug Taber’s Organic Chemistry Highlights [Supporting Information]

Mentored Publications:

10) Brailsford, J. A.;‡ Stockdill, J. L.;‡ Axelrod, A. J.; ‡* Peterson, M. T.; Vadola, P. A.; Johnston, E. V.; Danishefsky, S. J. Total Chemical Synthesis of Human Thyroid-Stimulating Hormone (hTSH) β-Subunit: Application of Arginine-tagged Acetamidomethyl (AcmR) Protecting Groups. Tetrahedron, 2018, 74, 1951–1956.

9) Bagdanoff, J. T.; Behenna, D. C.; Stockdill, J. L.; Stoltz, B. M.* Enantioselective Synthesis of Caprolactam and Enone Precursors to the Heterocyclic DEFG Ring System of Zoanthenol. Eur. J. Org. Chem. 2016, 2021–2024.

Untitled 00_StockdillLab_documents-18)  Wilson, R. M.; Stockdill, J. L.; Vadola, P. A.; Wu, X.; Li, X.; Park, P. K.; Wang, P.; Danishefsky, S. J. A Fascinating Journey into History: Exploration of the World of Isonitriles as Precursors to Complex Amides. Angew. Chem. Int. Ed. 2012, 51, 2834–2348. 7)  Wu, X.; Stockdill, J. L.; Park, P. K.; Danishefsky, S. J. Expanding the Limits of Isonitrile-Mediated Amidations Through a Second-Generation Synthesis of Cyclosporine: On the Remarkable Stereosubtleties of Macrolactam Formation from Seco-Cyclosporins. J. Am. Chem. Soc. 2012, 134, 2378–2384.

6)  Wu, X.; Stockdill, J. L.; Wang, P.; Danishefsky, S. J. Total Synthesis of Cyclosporine: Access to N-Methylated Peptides via Isonitrile Coupling Reactions. J. Am. Chem. Soc. 2010, 132, 4098–4100.

5)  Stockdill, J. L.; Wu, X.; Danishefsky, S. J. Coupling Reactions of Hindered Alkyl Thioacids and Hindered Isonitriles: Mechanistic Studies. Tetrahedron Lett. 2009, 50, 5152–5155.

4)  Stockdill, J. L.; Behenna, D. C.; McClory, A. M.; Stoltz, B. M. An Efficient Synthesis of the Carbocyclic Core of Zoanthenol. Tetrahedron, 2009, 65, 6571–6575. Invited paper for Tetrahedron Prize Special Issue

3)  Stockdill, J. L.; Behenna, D. C.; Stoltz, B. M.  Unexpected Decarbonylation During an Acid-Mediated Cyclization to Access the Carbocyclic Core of Zoanthenol. Tetrahedron Lett. 2009, 50, 3182–3184. Invited paper for 50th Anniversary Special Issue

2)  Behenna, D. C.; Stockdill, J. L.; Stoltz, B. M.  The Biology and Chemistry of the Zoanthamine Alkaloids. Angew. Chem. Int. Ed. 2008, 47, 2365–2386.

1)  Behenna, D. C.; Stockdill, J. L.; Stoltz, B. M. Synthesis of the Carbocyclic Core of Zoanthenol: Implementation of an Unusual Acid-Catalyzed Cyclization. Angew. Chem. Int. Ed. 2007, 46, 4077–4079.