Our one-pot strategies for making glycolipids are based upon the remarkable reactivity profile of glycosyl iodides. Once thought to be too reactive to be of synthetic value, studies from our lab and a few others throughout the world indicate quite the contrary. In fact, the unique reactivity of glycosyl iodides allows them to be generated in a single step from anomeric silyl ethers and subsequently reacted with fully functionalized ceramide, cholesterol and glycerol ester acceptors to provide immunogenic glycolipids with remarkable stereocontrol. This streamlined synthetic platform has enabled us to provide these materials to researchers throughout the world who are interested in characterizing the immunogenicity profiles of glycolipids.
a. Schombs, M., F.E. Park, W. Du, S.S. Kulkarni, J. Gervay-Hague. One-pot syntheses of immunostimulatory glycolipids. The Journal of Organic Chemistry. 2010, 75(15): 4891-8. DOI: 10.1021/jo100366v
b. Davis, R.A., C.H. Lin, J. Gervay-Hague. Chemoenzymatic synthesis of cholesteryl-6-O-tetradecanoyl-alpha-d-glucopyranoside: a product of host cholesterol efflux promoted by Helicobacter pylori. Chemical Communications (Cambridge, England). 2012, 48(72): 9083-5. DOI: 10.1039/C2CC33948J
c. Davis, RA, Fettinger, JC, Gervay-Hague, J. Tandem Glycosyl Iodide Glycosylation and Regioselective Enzymatic Acylation Affords 6-O-Tetradecanoyl-alpha-d-cholesterylglycosides. The Journal of Organic Chemistry. 2014, 79(17): 8447-52. DOI: 10.1021/jo501371h
d. Nguyen, HQ, Davis, RA, Gervay-Hague, J. Synthesis and Structural Characterization of Three Unique Helicobacter pylori alpha-Cholesteryl Phosphatidyl Glucosides. Angewandte Chemie (International ed. in English). 2014, 53 (49), 13400-13403. DOI:10.1002/anie.201406529
e. Lin, C-H., Jan, HM, Chen, YC, Shih, YY, Huang,YC, Tu, Z, Liu, S, Ingle, A, Wu, MS, Gervay-Hague, J., Mong, KT, Chen, Y. Metabolic Labelling of Cholesteryl Glucosides in Helicobacter pylori Reveals How Uptake of Human Lipids Enhances Bacterial Virulence. Chemical Science. 2016. DOI:10.1039/C6SC00889E
f. Lai, Alan Chuan-Ying, Chi, Po-Yu, Thio, Christina Li-Ping, Han, Yun-Chiann, Kao, Hsien-Neng, Hsieh, Hsioa-Wu, Gervay-Hague, Jacquelyn and Chang, Ya-Jen “α-Lactosylceramide Protects Against iNKT-Mediated Murine Airway Hyperreactivity and Liver Injury Through Competitive Inhibition of Cd1d Binding” Frontiers in Chemistry, 2019, Nov. 28, DOI.org/10.3389/fchem.2019.00811
g. Hau-Ming Jan, Yi-Chi Chen, Tsai-Chen Yang, Lih-Lih, Chia-Chen Chang, Sasikala Muthusamy, Andualem Bahiru Abera, Ming-Shiang Wu, Jacquelyn Gervay-Hague, Kwok-Kong Tony Mong, & Chun-Hung Lin “Cholesteryl-α-D-glucoside 6-acyltransferase enhances the adhesion of Helicobacter pylorito gastric epithelium” Nature, Comminications Biology, 2020, 3:120. DOI.org/10.1038/s42003-020-0855-y