Posted February 22, 2010
Revised March 14, 2010
Copyright © by YSU Center for Applied Chemical Biology
This web page does not work well with Internet Explorer. It does appear to work well with Firefox and Safari.
Posted February 22, 2010 Revised March 14, 2010 Copyright © by YSU Center for Applied Chemical Biology This web page does not work well with Internet Explorer. It does appear to work well with Firefox and Safari. |
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Research Description: Small Molecule Glycomimetics The Norris Group is mainly interested in synthetic heterocyclic chemistry, especially synthesis using carbohydrates as precursors. Our current projects include construction of analogs of the aminosugars found in the defensive capsular polysaccharide (CP) of Staphylococcus aureus (Figure 1) that may be capable of inhibiting CP construction and thus serving as antibiotics. The three sugars found in the repeating units of the most common strains of S. aureus (types 5 and 8) are the enantiomeric N-acetyl D- and L-fucosamines and N-acetyl-D-mannosamineuronic acid. We have recently solved the crystal structure of the N-acetyl-L-fucosamine fragment (Figure 2). In collaboration with Professor Diana Fagan in the Department of Biological Sciences, we are able to assay synthetic compounds as they are produced in order to study their potential as inhibitors of CP biosynthesis. We have several promising derivatives that have shown activity in suppressing capsule growth.  C-C Bond-forming Reactions on Sugars Derivatives such as branched-chain sugars are important components of antibiotics and related C-glycosides offer potential as non-hydrolyzable mimics of O-glycosides. We are exploring the use of carbenoid insertion chemistry in this area by building and decomposing sugar-linked diazo compounds, particularly on furanose scaffolds. Metal-catalyzed diazo decomposition leads to interesting products, including diastereomerically pure lactones through C-H insertion products where the carbenoid bites back into the carbohydrate framework (Figure 3). We are using this chemistry in the synthesis of several families of natural products including the plakortones and the canadensolides (Figure 4).  |
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Principle Investigators [links to research project descriptions and contact information for each PI] > Dr. David Asch > Dr. Ganesaratnam Balendiran > Dr. Jon Caguiat > Dr. Chet Cooper > Dr. Diana Fagan > Dr. Jozsi Jalics > Dr. Xiangjia Min > Dr. Peter Norris > Dr. Yogen Panta > Dr. Doug Price > Dr. Nina Stourman > Dr. Gary Walker > Mr. Rob Wardle > Dr. George Yates Other CACB Personnel > Staff > Graduate Students > Undergraduate Students > Alumni CACB Home The CACB in Detail > Center Concept > Scope of Activities > Technological Capabilities > Sponsored Research Projects > Faculty Research Groups > Collaborators |
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