Ph.D. University of California, Los Angeles
We are synthetic chemists developing vaccines and adjuvants to treat viral infection and cancer. Our research is focused on creating experimental methods for the efficient conjugation of site-specific functionalized peptides as vaccine candidates. In an effort to improve avidity and bioavailability, peptides directed against neutralizing antibodies have been successfully multimerized using a 1-3 dipolar cyclization strategy. Our central contributions involve introduction of a trialkyne functionality onto rigid scaffolds that promote the cyclization process. The synthesis of glycolipid natural products complements the vaccine design program. One-pot synthetic routes for large quantity production of alpha-galactosyl ceramides, cholesteryl glycosides and glycerol containing glycolipds using glycosyl iodide chemistry have been established. This synthetic chemistry platform exploits the unique reactivity of glycosyl iodides providing highly efficient routes to immunostimulatory glycolipids for adjuvant therapy. Further developments in step-economy synthesis of tumor associated carbohydrate antigens (TACAs) have been achieved using Regioselective Silyl Exchange Technology (ReSET); a synthetic process, which minimizes the need for elaborate protecting group strategies to build complex oligosaccharides. Instead, per-O-silylated sugars undergo selective exchange of silicon protecting groups giving orthogonally protected carbohydrate building blocks in as few as two steps. Integration of the ReSET strategy with the unique reactivity of glycosyl iodides provides a powerful platform for glycolipidomic profiling.
Education, Awards and Professional Highlights
- Director, Division of Chemistry, NSF (2013-2014)
- Fellow, American Association for the Advancement of Science (AAAS) (2012)
- Chair, Department of Chemistry, UC Davis (2011-2013)
- Associate Vice Provost, UC Davis (2009-2011)
- Fellow, The American Chemical Society (2009)
- Board of Editors, Organic Reactions (2006-2012)
- Associate Editor, Journal of Organic Chemistry (2003-2013 and 2015 to present)
- Chair, Carbohydrates Gordon Conference (2003)
- Vice Chair of Carbohydrates GRC (2001)
- NIH, Med Chem A Study Section Member (2001-2005)
- Editorial Board, Journal of Carbohydrate Chemistry (2001-2006)
- Editorial Board, Carbohydrate Research (2000-2006)
- ACS, Division of Carbohydrate Chemistry Officer (1999-2004)
- Appointed to UC Davis faculty (2001)
- Appointed Onsite Consultant Roche Biosciences (2000)
- GenCorp 1999 Technology Achievement Award (1999)
- Horace Isbell Award, Carbohydrate Division of ACS (1999)
- Associate Professor, University of Arizona (1998)
- Alfred P. Sloan Fellow (1998)
- NSF CAREER Award (1997)
- Eli Lilly Academic Awardee (1997)
- Appointed Assistant Professor, University of Arizona (1992)
- NIH Postdoctoral Fellow, Yale University (1990-1992)
- Ph.D. UCLA (1990)
- Saul Winstein Dissertation Awardee, UCLA (1989)
- B.S. UCLA (1985)
- University President's Fellowship, UCLA (1984-1985)
“Solution phase conformation and proteolytic stability of amide‐linked neuraminic acid analogues”
JP Saludes, TQ Gregar, IA Monreal, BM Cook, LM Danan‐Leon, J Gervay‐Hague
Biopolymers 2013, 10, 686-696.
“Synthesis and Structural Characterization of Sialic Acid− Glutamic Acid Hybrid Foldamers as Conformational Surrogates of α-2, 8-Linked Polysialic Acid”
JP Saludes, JB Ames, J Gervay-Hague
Journal of the American Chemical Society 2009, 131 (15), 5495-5505.
“Construction of di-scFv through a trivalent alkyne–azide 1, 3-dipolar cycloaddition”
A Natarajan, W Du, CY Xiong, GL DeNardo, SJ DeNardo, J Gervay-Hague
Chemical Communications 2007, 695-697.
“A general chemical synthesis platform for crosslinking multivalent single chain variable fragments”
JG Schellinger, A Kudupudi, A Natarajan, W Du, SJ DeNardo, J Gervay-Hague
Organic & Biomolecular Chemistry 2012, 10 (8), 1521-1526.
“Synthesis of a trimeric gp120 epitope mimic conjugated to a T-helper peptide to improve antigenicity”
JG Schellinger, LM Danan-Leon, JA Hoch, A Kassa, I Srivastava, D Davis, J Gervay-Hague
Journal of the American Chemical Society 2011, 133 (10), 3230-3233.
“Regioselective Silyl/Acetate Exchange of Disaccharides Yields Advanced Glycosyl Donor and Acceptor Precursors”
HW Hsieh, MW Schombs, MA Witschi, J Gervay-Hague
The Journal of Organic Chemistry 2013, 78, 9677-9688.
“Chemoenzymatic synthesis of cholesteryl-6-O-tetradecanoyl-α-d-glucopyranoside: a product of host cholesterol efflux promoted by Helicobacter pylori”
RA Davis, CH Lin, J Gervay-Hague
Chemical Communications 2012, 48 (72), 9083-9085.
“One-Pot Syntheses of Immunostimulatory Glycolipids”
M Schombs, FE Park, W Du, SS Kulkarni, J Gervay-Hague
The Journal of Organic Chemistry 2010, 75 (15), 4891-4898
“Selective Acetylation of per-O-TMS-Protected Monosaccharides”
MA Witschi, J Gervay-Hague
Organic Letters 2010, 12 (19), 4312-4315.
“Two-Step Synthesis of the Immunogenic Bacterial Glycolipid BbGL1”
SS Kulkarni, J Gervay-Hague
Organic Letters 2008, 10 (21), 4739-4742