Abstract: O-Cyanoethylations have been extended to cyclodextrin derivatives. It was found the alcohols at the primary face of cyclodextrins readily react to add to acrylonitrile. See: R. Ghosh, M. Bhowmick, P. Zhang and C.-C. Ling, Can. J. Chem. , 94, 436-443 (2016). Univ. of Calgary 50 years special issue.
A synthetic peracetylated 4-fluoro-glucosamine has been shown to inhibit the biosynthesis of chondroitin sulfate proteoglycans (CSPGs), which could provide a useful strategy to promote repair in multiple sclerosis and other neurological disorders, by reducing deposition of CSPGs into the lesion microenvironment. See: 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.
An efﬁcient O3-monodesilylation method has been developed using HCl to per-3-O-silylated cyclodextrin derivatives. See: J. Gu, T. Chen, Q. Wang and C.-C. Ling, Carbohydr. Res., 410, 36-46 (2015).
A controlled HCl-mediated O-desilylation method has been developed from the easily accessible per-3,6-O-silylated CD derivatives. Unprecedented regioselectivity has been observed during the course of O-desilylations. See: J. Gu‡, T. Chen‡, P. Zhang and C.-C. Ling, Eur. J. Org. Chem., 5793-5805 (2014).
The ability of amphiphilic clodextrin derivatives to form self-organized thermotropic mesophases correlates with their ability to form intermolecular hydrogen bonds. See: 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).
A mechanistic study on the di-inversion of 2,3-di-O-sulfonates of glycopyranosides provided direct evidence of the unusual O-transsulfonylations. Alkali cations were found to facilite the initial attack by regioselective actvating the sulfonate that has a neighboring cis-oxygen. see: R. Hevey and C.-C. Ling, Org. Biolmol. Chem., 11, 1887-1895 (2013).
DIBAL-H mediated O-desilylation has been found to be regioselective for cyclodextrins. See: R. Ghosh, P. Zhang, A. Wang, C.-C. Ling, Angew. Chem. Int. Ed., 51, 1548-1552 (2012)
An efficient route as been developed to obtain the challenging β-idopyranosides which is expressed by Campylobacter jejuni. See: R. Hevey, A. Morland and C.-C. Ling, J. Org. Chem., 77, 6760-6772 (2012).
We reported the first per-tritylation at the primary face of cyclodextrins. See: P. Zhang, A. Wang, L. Cui and C.-C. Ling, Org. Lett., 14, 1612-1615 (2012).
A novel glycal that consists of an 1-C-aryl fragment has been developed. The glycal was found to be highly efficient to obtain β-Kdo glycosides. See: Y. Qian, J. Feng and C.-C. Ling, J. Org. Chem., 77, 96-107 (2012).
Due to inherent problems associated with lower reactivity of secondary hydroxyl groups, the chemical perfunctionalization at the secondary face of cyclodextrins has met less success in the literature. Cu(I)-mediated Huisgen 1,3-dipolar cyclization was found to be efficient to introduce a variety of functional groups to the secondary face of cyclodextrins. see: S. Ward, C.-C. Ling, Eur. J. Org. Chem., 4853-4861 (2011).
A novel class of structurally well-defined nanotubes from β-cyclodextrin is reported. These new hosts have a deep hydrophobic channel of more than 1.5 nm long. See: A. Wang, W. Ling, P. Zhang, C.-C. Ling, Org. Lett., 13, 3572-3575 (2011).
A Lewis A-LacNAc pentasaccharide has been synthesized to probe the binding site of TcdA of the multidrug resistant Clostridium difficile. See: P. Zhang, K. Ng and C.-C. Ling, Org. Biomol. Chem., 8, 128-136 (2010).
The Substrate specificity for human bifunctional enzyme, the α(1,3)/(1,4)-fucosyltransferase has been clarified. See: 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).
The binding site of Campylobacter jejuni CST-II enzyme has been probed using synthetic substrates. This lead to an efficient chemoenzymatic synthesis of the most challenging α(2,8)-linked oligosialosides. See: P. Zhang, A. J. Zuccolo, W. Li, R. B. Zheng and C.-C. Ling, Chem. Commun., 4233-4235 (2009) and W. Li, P. Zhang, A. J. Zuccolo, R. B. Zheng and C.-C. Ling, Carbohydr. Res., 346, 1692-1704 (2011).