T. Bruce Grindley 

Professor

BSc, MSc, PhD (Queen's)

E-mail: bruce.grindley@dal.ca
Phone: (902) 494-2041
Fax: (902) 494-1310

Research Interests: Organic Chemistry. 

The research interests of Dr. Grindley's group centre around carbohydrates and include many associated topics.  Organic synthesis is key to most projects and discovering new ways to make interesting molecules is an enduring theme. 

Other themes that run through the group's projects are NMR spectroscopy, stereochemistry, conformational analysis, and molecular modeling. Two active projects deal with carbohydrates on cell surfaces.  Cell surface carbohydrates play important biological roles in the recognition of many species, such as viruses, antibodies, toxins, enzymes, etc. but other roles are not well understood.  Urinary tract infections (UTI) are initiated by the binding of a protein FimH at the tip of pili of uropathegenic strains of E. coli to mannose-terminated oligosaccharides on a glycoprotein, uroplakin Ia, one of the major constituents of the surface of the urinary tract.  Initial binding triggers a conformational change in the surface that allows the bacteria to bind via a shear-force enhanced catch-bond mechanism and then establish colonies beneath the surface.  The group is synthesizing glycodendrimers and dendronized polymers to produce compounds that bind multiple pili on the bacterial surface better than does the natural ligand.  It is hoped that this "anti-adhesion" strategy can help to cure persistant UTIs, the second most diagnosed disease in North America. Another interest is in Lyme disease, which  is expanding northward in North America Europe and Asia.  This disease is caused by a spirochete bacteria, Borrelia burgdorferi, that is mainly carried by black-legged ticks. Part of its bacterial cell surface consists of glycolipids and two specific glycolipids have been shown to be sufficiently antigenic to serve as the basis of vaccines.  The group is developing methods for the synthesis of variants of the antigenic glycolipids to define the structural criteria critical for antigenicity with the aim of producing vaccines in which multiple copies of the antigens are carried by dendrimers or dendronized proteins.

The development of synthetic methods involving carbohydrates is an important aspect of the group's interests. Dialkylstannylene acetals are valuable intermediates for the regioselective monosubstitution of diols or polyols which is critical for successful carbohydrate synthesis.  The group has made significant contributions to the improvement of reactions involving dibutylstannylene acetals and in understanding why they give good regiochemical control. Current efforts emphasize examining reaction pathways by computational methods and intermediate structures by 1D and 2D multinuclear (119Sn, 19F, 13C, and 1H) NMR methods.  Another area that the group is involved with is the synthesis of gemini surfactants.  Pentaerythritol-based gemini surfactants have been discovered that have excellent properties and glycerol-based surfactants are currently being investigated.