Title

Towards the Synthesis of a C-glycoside Tn Antigen

Submitter Information

Advait DesaiFollow

Type of Proposal

Oral Presentation

Start Date

22-3-2018 10:55 AM

End Date

22-3-2018 12:15 PM

Location

Alumni Auditorium A

Faculty

Faculty of Science

Faculty Sponsor

Dr. Trant

Abstract/Description of Original Work

Towards the Synthesis of a C-glycoside Tn Antigen Advait Desai, Iraj Sadraei, John F. Trant Many biological processes including bacterial and viral infections (notably HIV and the flu), immunogenic responses, and cancer pathogenesis/metastasis are mediated by carbohydrate interactions. An example of such a carbohydrate is the Tn antigen. The Tn antigen is particularly interesting as it shows up in a large number of different cancer cells including: gastric, colon, breast, lung, esophageal, prostate, and endometrial cancer. If the immune system could be trained to target this molecule, then the immune system could be used to help cure cancer. A key drawback to using this method is the inherent low in vivo half-lives of carbohydrate containing materials. This Trant Team project aims to remove the unstable acetal functionality of the Tn antigen by replacing the exocyclic anomeric oxygen with a methylene (C-glycoside) to make new acetal-free C-glycoside analogues of the Tn antigen. Removing the labile functionality should result in greatly enhanced lifetime, and bioavailability relative to the native system with no loss of activity as the exocyclic oxygen is not involved in the vast majority of molecular recognition events. This molecule is being made by total synthesis for its incorporation into new anti-cancer vaccines.

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Mar 22nd, 10:55 AM Mar 22nd, 12:15 PM

Towards the Synthesis of a C-glycoside Tn Antigen

Alumni Auditorium A

Towards the Synthesis of a C-glycoside Tn Antigen Advait Desai, Iraj Sadraei, John F. Trant Many biological processes including bacterial and viral infections (notably HIV and the flu), immunogenic responses, and cancer pathogenesis/metastasis are mediated by carbohydrate interactions. An example of such a carbohydrate is the Tn antigen. The Tn antigen is particularly interesting as it shows up in a large number of different cancer cells including: gastric, colon, breast, lung, esophageal, prostate, and endometrial cancer. If the immune system could be trained to target this molecule, then the immune system could be used to help cure cancer. A key drawback to using this method is the inherent low in vivo half-lives of carbohydrate containing materials. This Trant Team project aims to remove the unstable acetal functionality of the Tn antigen by replacing the exocyclic anomeric oxygen with a methylene (C-glycoside) to make new acetal-free C-glycoside analogues of the Tn antigen. Removing the labile functionality should result in greatly enhanced lifetime, and bioavailability relative to the native system with no loss of activity as the exocyclic oxygen is not involved in the vast majority of molecular recognition events. This molecule is being made by total synthesis for its incorporation into new anti-cancer vaccines.