Research

Independent Peer-Reviewed Publications

Multi-responsive self-assembled pyrene-appended β-cyclodextrin nanoaggregates: discriminative and selective ratiometric detection of pirimicarb and trinitro-explosives. Pier-Luc Champagne,§ Rajesh Kumar,§ and Chang-Chun Ling, Submitted (2018).

Synthesis and Unprecedented Complexation Properties of β-Cyclodextrin-based for Lanthanide Metals. Pierre-Luc Champagne,§ Cécile Barbot,§ Ping Zhang, Xuekun Han, Issam Gaamoussi, Marie-Hubert Roux, Gabriel E. Bertolesi, Gouhier Géraldine and Chang-Chun Ling, Inorganic Chemistry, 57, 8964-8977 (2018). DOI: 10.1021/acs.inorgchem.8b00937..

Chondroitin sulfate proteoglycans as novel drivers of leukocyte infiltration in multiple sclerosis. Erin Stephenson, Manoj Mishra, Daniel Moussienko, Nataly Laflamme, Serge Rivest, Chang-Chun Ling, V. Wee Yong, Brain, 141, 1094-1110 (2018). Doi: 10.1093/brain/awy033

Synthesis and Comparison of Mesomorphic Behavior of a Cholesterol-based Liquid Crystal Dimer and Analogous Monomers. Pier-Luc Champagne, David Ester, Salem Aldosary, Vance E. Williams and Chang-Chun Ling, Liquid Crystals, published (2017). Doi: 10.1080/02678292.2017.1417505.

Clustering of Pk-trisacharide on Amphiphilic Cyclodextrin Reveals Unprecedented Affinity for the Shiga-like Toxin, Stx2. Ping Zhang, Eugenia Paszkiewicz, Qifang Wang, Joanna M. Sadowska, Pavel I. Kitov, David R. Bundle and Chang-Chun Ling, Chem. Commun., 53, 10528-10531 (2017). Doi: 10.1039/C7CC06299K.

Total Synthesis of β-D-Ido-heptopyranosides Related to the Capsular Polysaccharides of Campylobacter jejuni HS:4. P. Zhang, R. Hevey and C.-C. Ling, J. Org. Chem., 82(18), 9662-9674 (2017). Doi: 10.1021/acs.joc.7b01752.

Inverting Substitution Patterns on Amphiphilic Cyclodextrins Induces Unprecedented Formation of Hexagonal Columnar Superstructures. Pier-Luc Champagne, David Ester, Michael Zeeman, Carson Zellman, Vance E. William and Chang-Chun Ling, J. Mat. Chem. C, 5, 9247-9254 (2017). Doi: 10.1039/C7TC02636F. Featured as a hot paper, and also front cover of the issue.

The role of multilayers in preventing the premature buckling of the pulmonary surfactant. Mustafa Al-Saiedy, Ali Tarokh, Sultan Nelson, Kiavash Hossini, Francis Green, Chang-Chun Ling, Elmar J. Prenner and Matthias Amrein, Biochimica et Biophysica Acta (BBA) - Biomembranes, 1859(8), 1372-1380 (2017). Doi: 10.1016/j.bbamem.2017.05.004.

Studies on the 6-Homologation of β-D-Idopyranosides. Rachel Hevey, Chang-Chun Ling, Carbohydr. Res., 445, 65-74 (2017). Doi: 10.1016/j.carres.2017.04.007.

A Mild Acetolysis Procedure for the Regioselective Removal of Isopropylidene in Di-O-isopropylidene-protected Pyranoside Systems. Pengfei Zhang and Chang-Chun Ling, Carbohydr. Res., 445, 7-13 (2017). Doi: 10.1016/j.carres.2017.03.021.

First Family of Amphiphilic Cyclodextrin Liquid Crystals Driven by Dipole-Dipole Interactions. P.-L. Champagne, D. Ester, S. Ward, V. E. Williams, C.-C. Ling, ChemPlusChem 82(3), 423-432 (2017). Doi: 10.1002/cplu.201600556.

Synthesis of Rationally Designed Tetrasaccharides for Crystallographic and Binding Studies with Clostridium difficile Toxins and Unexpected Partial N-methylations during Catalytic Hydrogenation of Azides in Methanol. P. Zhang, K. Ng, C.-C. Ling, Can. J. Chem., 94(11), 961-968 (2017). DOI: 10.1139/cjc-2016-0226. Bundle Special Issue.

Inhibition of chondroitin sulfate proteoglycan synthesis promotes central nervous system remyelination. M. B. Keough, J. A. Rogers, P. Zhang, S. K. Jensen, E. L. Stephenson, T. Chen, M. G. Hurlbert, L. W. Lau, K. S. Rawji, J. R. Plemel, M. Koch, C.-C. Ling, V. W. Yong, Nat. Commun. , 7, 11312. DOI: 10.1038/ncomms11312

Cyanoethylation of Cyclodextrin Derivatives. R. Ghosh, M. Bhowmick, P. Zhang and C.-C. Ling, Can. J. Chem. , 94, 436-443 (2016). Univ. of Calgary 50 years special issue.

Genetically Encoded Fragment-Based Discovery of Glycopeptide Ligands for Carbohydrate-Binding Proteins. S. Ng, E. Lin, P. I. Kitov, K. F. Tjhung, O. O. Gerlits, L. Deng, B. Kasper, A. Sood, B. M. Paschal, P. Zhang, C.-C. Ling, J. S. Klassen, C. J. Noren, L. K. Mahal, R. J. Woods, L. Coates, and R. Derda, J. Am. Chem. Soc., 137, 5248-5251 (2015).

Efficient Regioselective O3-Monodesilylation by Hydrochloric Acid in Cyclodextrins Carbohydrate Research. J. Gu, T. Chen, Q. Wang and C.-C. Ling, Carbohydr. Res., 410, 36-46 (2015).

Addressing the global need to combat multi-drug resistance, carbohydrates may hold the key. Q. Wang and C.-C. Ling, Future Med. Chem., 6, 1539-1543 (2014). (Invited Editorial)

Synthesis of modified Trichinella spiralis disaccharide epitopes and a comparison of their recognition by chemical mapping and saturation transfer difference NMR. L. Cui, C.-C. Ling, J. Sadowska, D. R. Bundle, Carbohydr. Res., 383, 1-13 (2014).

Controlled Acid-mediated Regioselective O-Desilylations for Multi-functionalization of Cyclodextrins. J. Gu,# T. Chen,# P. Zhang and C.-C. Ling, Eur. J. Org. Chem., 5793-5805 (2014).

Investigation into the Role of the Hydrogen Bonding Network in Cyclodextrin-based Liquid Crystals. S. Ward, O. Calderon, P. Zhang, M. Sobchuk, S. N. Keller, V. Williams and C.-C. Ling, J. Mater. Chem. C, 2, 4928-4936 (2014).

Role of the 4,6-O-acetal in the regio- and stereoselective conversion of 2,3-di-O-sulfonyl-β-D-galactopyranosides to D-idopyranosides. R. Hevey, X. Chen and C.-C. Ling, Carbohydr. Res., 376, 37-48 (2013).

Synthesis of P-Triazole Dithienophospholes and a Cyclodextrin-based Sensor via Click Chemistry. X. He, P. Zhang, J.-B. Lin, H. V. Huynh, S. E. N. Munoz, C.-C. Ling and T. Baumgartner, Org. Lett., 15, 5322-5325 (2013).

Recent advances toward the development of inhibitors to attenuate tumor metastasis via the interruption of lectin-ligand interactions. R. Hevey and C.-C. Ling, Adv. Carbohydr. Chem. Biochem., 69, 126-207 (2013).

DIBAL-H-mediated O-desilylation with highly sterically hindered cyclodextrin substrates. R. Ghosh, C. Hennigan and C.-C. Ling, Tetrahedron, 69, 5227-5233 (2013).

Evidence of Cation-Coordination Involvement in Directing the Regioselective Di-Inversion Reaction of Vicinal Di-Sulfonate Esters. R. Hevey and C.-C. Ling, Org. Biolmol. Chem., 11, 1887-1895 (2013).

Formation, Spectroscopic Characterization, and Solution Stability of an [Fe4S4]2+ Derived from b-Cyclodextrin Dithiolate. W. Lo, P. Zhang, C.-C. Ling, S. Huang and R. Holm, Inorg. Chem., 51, 9883-9892 (2012).

A Scalable Approach to Obtaining Orthogonally Protected β-D-Idopyranosides. R. Hevey, A. Morland and C.-C. Ling, J. Org. Chem., 77, 6760-6772 (2012). Selected by the Editor as a featured article.

First Per-6-O-tritylation of Cyclodextrins. P. Zhang, A. Wang, L. Cui and C.-C. Ling, Org. Lett., 14, 1612-1615 (2012).

Recent Advances in Developing Synthetic Carbohydrate-based Vaccines for Cancer Immunotherapies. R. Hevey and C.-C. Ling, Fut. Med. Chem., 4, 545-584 (2012).

Diisobutylaluminum Hydride-Mediated Regioselective O-Desilylations as a Novel Route to Access Multisubstituted Cyclodextrins. R. Ghosh, P. Zhang, A. Wang, C.-C. Ling, Angew. Chem. Int. Ed., 51, 1548-1552 (2012). Ranked as very important paper. Chosen by Editor as a Hot Paper. Highlighted as a Frantispeice in the journal.

The Unexpected Anomeric Selectivity for Kdo Glycoside Syntheses Using 1-C-Aryl-glycals as a Donor. Y. Qian, J. Feng and C.-C. Ling, J. Org. Chem., 77, 96-107 (2012).

Global Financial Challenge: Opportunities for Strengthening R&D Research in Targeted Drug Delivery. R. Hevey, C.-C. Ling, Fut. Med. Chem., 4, 1-5 (2012).

Synthesis of a Forssman Antigen Derivative for Use in a Conjugate Vaccine. J. Feng, R. Hevey, C.-C. Ling, Carbohydr. Res., 345, 2650-2662 (2011).

Unexpected structure of a C. difficile toxin A ligand necessitates an annotation correction in a popular screening library. P. Zhang, N. Razi, L. Eugenio, M. Fentabil, E. Kitova, J. Klassen, D. R. Bundle, K. K.-S. Ng and C.-C. Ling, Chem. Commun., 47, 12397-12399 (2011).

Synthesis of a Novel Class of Biodegradable Nanocages. A. Wang, W. Ling, P. Zhang, C.-C. Ling, Org. Lett., 13, 3572-3575 (2011). Highlighted.

Efficient and Versatile Modification of the Secondary Face of Cyclodextrins via Copper-Catalyzed Huisgen 1,3-Dipolar Cycloaddition. S. Ward, C.-C. Ling, Eur. J. Org. Chem., 4853-4861 (2011).

CST-II's Recognition Domain for Acceptor Substrates in α(2,8)-Sialylations. W. Li, P. Zhang, A. J. Zuccolo, R. B. Zheng and C.-C. Ling, Carbohydr. Res., 346, 1692-1704 (2011).

Alum interaction with dendritic cell membrane lipids is essential for its adjuvanticity. T. L. Flach, G. Ng, A. Hari, M. D. Desrosiers, Y. Fong, P. Zhang, S. M. Ward, M. E. Seamone, E. Prenner, C.-C. Ling, J. Tschopp, D. A. Muruve, M. W. Amrein, Y. Shi, Nature Medicine, 17, 479-487 (2011).

Eliciting an Carbohydrate-specific Immune Response against Sialosides: Success and Challenges C.-C. Ling and D. R. Bundle, Fut. Med. Chem., 3, 519-534 (2011).

Stabilities of Cubane Type [Fe4S4(SR)4]2- Clusters in Partially Aqueous Media. W. Lo, T. A. Scott, P. Zhang, C. -C. Ling and R. H. Holm, J. Inorg. Biochem., 105, 497-508 (2011).

An Efficient Conversion of N-Acetyl-D-glucosamine to N-Acetyl-D-galactosamine and Derivatives. J. Feng and C.-C. Ling, Carbohydr. Res., 345, 2450-2457 (2010).

Controlled Synthesis of Linear α-Cyclodextrin Oligomers Using Copper-catalyzed Huisgen 1,3-Dipolar Cycloaddition. G. K. Rawal, P. Zhang and C.-C. Ling, Org. Lett., 12, 3096-3099 (2010).

DIBAL-H mediated triple and quadruple debenzylations reactions of perbenzylated cyclodextrins. G. K. Rawal, S. Rani, S. Ward and C.-C. Ling, Org. Biomol. Chem., 8, 171-180 (2010).

Efficient synthesis of LeA-LacNAc pentasaccharide as a ligand for Clostridium difficile toxin A. P. Zhang, K. Ng and C.-C. Ling, Org. Biomol. Chem., 8, 128-136 (2010).

Exploiting a Sialyltransferase's Ability to Recognize a New Class of Acceptors to Prepare α(2,8)-Oligosialosides and Analogs. P. Zhang, A. J. Zuccolo, W. Li, R. B. Zheng and C.-C. Ling, Chem. Commun., 4233-4235 (2009).

Unexpected Tri- and Tetra-debenzylation of Perbenzylated α-Cyclodextrin. G. K. Rawal, S. Rani and C.-C. Ling, Tetrahedron Lett., 50, 4633-4636 (2009).

The conformation of a tetratritylated α-cyclodextrin with unusual proton NMR. S. Ward, P. Zhang and C.-C. Ling, Carbohydr. Res., 344, 808-814 (2009).

Receptor-independent, direct membrane binding leads to cell surface lipid sorting and dendritic cell phagocytic activities. G. Ng, K. Sharma, S. M. Ward, M. D. Desrosiers, L. A. Stephens, W. M. Schoel, T. Li, C. A. Lowell, C.-C. Ling, M. W. Amrein, and Y. Shi, Immunity, 29, 807-818 (2008).