Jennifer L Stockdill (fc0425)

 Chemistry

Chem 277

Synthesis of natural products, methodology development, synthesis and selective functionalization of peptides and proteins

Research in the Stockdill group is focused on the design of efficient strategies for the synthesis of biologically molecules ranging in structure from polycyclic alkaloids to disulfide-linked mini-proteins and macrocyclic polypeptides. In the course of these efforts, we explore chemical reactivity and develop new reaction methods.

Agency: Eli Lilly and Company, Lilly Research Award Program
Title: Strategies for Greener Peptide Synthesis
Status: Stockdill (P.I.), Kopach (internal Lilly collaborator)
Amount: $265,000 total costs
Start/End Date: 08/17/19-08/16/21

Agency: National Institutes of Health (R01)
Title: Strategies for N to C Solid-Phase Peptide Synthesis
Status: Stockdill (single P.I.)
Amount: $950,000 direct costs ($1,152,273 total costs)
Start/End Date: 09/01/19-05/31/23

Agency: ACS GCI Pharmaceutical Roundtable
Title: Catalytic Desulfurization of Peptides
Status: Stockdill (single P.I.)
Amount: $50,000 total costs (IC charged at 9.9%)
Start/End Date: 01/01/19-12/31/19

Agency: ACS GCI Pharmaceutical Roundtable
Title: A green strategy for the synthesis of head-to-tail macrocyclic peptides
Status: Stockdill (single P.I.)
Amount: $50,000 total costs (IC charged at 9.9%)
Start/End Date: 01/01/18-12/31/18

Agency: National Science Foundation (CAREER)
Title: CAREER: Harnessing the reactivity neutral aminyl radicals for complex heterocycle synthesis
Grant Number: CHE-1554752
Status: Stockdill (single P.I.)
Amount: $649,999 total costs
Start/End Date: 05/01/16-04/30/21

Agency: National Institutes of Health – NIGMS
Title: C–N Bond-Forming Methodologies for the Synthesis of Small Molecules and Peptides
Grant Number: R00-GM097095
Status: Stockdill (single P.I.)
Amount: $491,448 direct costs
Start/End Date: 09/17/12–09/16/15

Agency: National Institutes of Health – NIGMS
Title: C–N Bond-Forming Methodologies for the Synthesis of Small Molecules and Peptides (Minority Supplement to Above R00)
Grant Number: R00GM097095-S1
Status: Stockdill (single P.I.)
Amount: $75,712 direct costs
Start/End Date: 09/17/2012–09/16/2015

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. 

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. 

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.

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.

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.

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.

Arbour, C. A.;‡ Stamatin, R. E.;‡ Stockdill, J. L.* Divergent C-Terminal Elongation of Peptides. J. Org. Chem. 2018, 83, 1797–1803.

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, Amides, and Esters. Chem. Sci. 2018, 9, 350–355.

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.

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.

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.

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.

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 Prof. Harry Wasserman.

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.