Jennifer Stockdill

Jennifer Stockdill

Associate Professor

313-577-2605

313-577-8822 (fax)

stockdill@wayne.edu

Chem 277

Website(s)

http://stockdillgroup.info/

Social media

@StockdillLab

Jennifer Stockdill

Department

 Chemistry

Research interest(s)/area of expertise

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

Research

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.

Education

  • BS Virginia Tech 2003
  • PhD California Institute of Technology (Stoltz) 2009
  • NIH Postdoctoral Fellow, Memorial Sloan-Kettering Cancer Center 2009-2012

Awards and grants

  • 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

Selected publications

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.

Currently teaching

  • CHM 2220 Organic Chemistry II, 4 credit hours, W2020
    CHM 2225 Organic Chemistry II for Engineers, 3 credit hours, W2020
    CHM 5998 Honors Thesis Research in Chemistry, 2-4 credit hours, W2020
    CHM 5999 Research in Chemistry, 2-4 credit hours, W2020
    CHM 8810 Seminar in Organic Chemistry, 1 credit hour, W2020

     

Courses taught

CHM 5510 Chemical Synthesis Laboratory, 3 credit hours, F2019
CHM 5998 Honors Thesis Research in Chemistry, 2-4 credit hours, F2019
CHM 5999 Research in Chemistry, 2-4 credit hours, F2019
CHM 8810 Seminar in Organic Chemistry, 1 credit hour, F2019