Title

56. Synthesis of Tumor-Associated Carbohydrates Using Lewis Acid Catalysts

Presenter Information

Rania SalebFollow

Faculty Mentor(s)

Shailesh Ambre & Patricia Todebush

Campus

Gainesville

Proposal Type

Poster

Subject Area

Chemistry

Location

Floor

Start Date

22-3-2019 11:00 AM

End Date

22-3-2019 12:00 PM

Description/Abstract

Cancer is a collection of diseases that result from uncontrolled cell division to form tumorous tissue. Benign tumors are localized to a specific part and can be removed surgically. However, malignant tumors undergo a process called metastasis to migrate to neighboring or distant tissues from their original site of occurrence. Since malignant tumors invade other tissues they are hard to detect and difficult to treat. According to the National Cancer Institute, 1.7 million cases of cancer were reported in 2014. Unfortunately, these numbers are on the rise and effective therapies against cancer are desired and extensively investigated. The tumor cells differ from normal cells with respect to certain genes, proteins and also various sugars (tumor-associated carbohydrates). The changes to the polymeric structure of the cell-surface carbohydrates upon malignant transformation are well-documented. These changes play a critical role in the metastasis of tumor cells. The identification of these biomarkers and their isolation or synthesis are vital to investigate methods for early diagnosis and effective treatments of cancer. A major hurdle in advancing the research on TACs is the limited availability of these molecules in good quality and sufficient quantity. Chemical synthesis provides a solution by systematically building well-characterized molecules. However, most synthetic methods for making TACs are limited in terms of efficiency and scalability. Hence, there is a need to develop scalable & efficient protocols. Heterogeneous catalysis has a long history in synthetic chemistry and widely used industrially. These catalysts can be engineered to install sugars on amino acid sidechains in specific orientations. We have tested and compared different Lewis acids with commercially available glucose- and galactose-pentaacetate. Zirconium sulfate showed the cleanest results in model reaction systems. This poster highlights our continued efforts on screening more Lewis acids and their selectivity in installing these sugars on serine and threonine amino acids.

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Mar 22nd, 11:00 AM Mar 22nd, 12:00 PM

56. Synthesis of Tumor-Associated Carbohydrates Using Lewis Acid Catalysts

Floor

Cancer is a collection of diseases that result from uncontrolled cell division to form tumorous tissue. Benign tumors are localized to a specific part and can be removed surgically. However, malignant tumors undergo a process called metastasis to migrate to neighboring or distant tissues from their original site of occurrence. Since malignant tumors invade other tissues they are hard to detect and difficult to treat. According to the National Cancer Institute, 1.7 million cases of cancer were reported in 2014. Unfortunately, these numbers are on the rise and effective therapies against cancer are desired and extensively investigated. The tumor cells differ from normal cells with respect to certain genes, proteins and also various sugars (tumor-associated carbohydrates). The changes to the polymeric structure of the cell-surface carbohydrates upon malignant transformation are well-documented. These changes play a critical role in the metastasis of tumor cells. The identification of these biomarkers and their isolation or synthesis are vital to investigate methods for early diagnosis and effective treatments of cancer. A major hurdle in advancing the research on TACs is the limited availability of these molecules in good quality and sufficient quantity. Chemical synthesis provides a solution by systematically building well-characterized molecules. However, most synthetic methods for making TACs are limited in terms of efficiency and scalability. Hence, there is a need to develop scalable & efficient protocols. Heterogeneous catalysis has a long history in synthetic chemistry and widely used industrially. These catalysts can be engineered to install sugars on amino acid sidechains in specific orientations. We have tested and compared different Lewis acids with commercially available glucose- and galactose-pentaacetate. Zirconium sulfate showed the cleanest results in model reaction systems. This poster highlights our continued efforts on screening more Lewis acids and their selectivity in installing these sugars on serine and threonine amino acids.