Project Overview

Organic Synthesis of a Tumor-Associated Carbohydrate Antigen Mimic for Immunological Studies

Faculty Sponsor

Ernie Nolen (enolen@colgate.edu)

Department(s)

Chemistry

Abstract

Our primary goal is the development of useful synthetic glycopeptide mimics that effectively represent tumor cell surface O-glycopeptides such as the alpha-linked O-GalNAc Ser/Thr. These mimics will provide metabolic stability to enhance bioavailability, and are expected to have altered binding affinities to immune surveillance molecules that may help break inherent immunotolerance. 
 
We herein propose to synthesize pure, robust mimics of Tn antigen (a tumor-associated carbohydrate antigen) with conformational realism, as they may be presented from the backbone of biomedically relevant peptides and to compare these mimics with Tn antigen itself, by NMR and molecular dynamics simulations for clarification of the essential structural features necessary to maximize biological activity.  The most promising mimics will be incorporated into peptide sequences for immunological and tumor inhibition studies by collaborators.  The work at Colgate entails multi-step organic synthesis and characterization of reaction products by NMR and mass spectrometry.
 

Student Qualifications

Completion of CHEM 264 and plans to major in CHEM  or BIOC.

Number of Student Researchers

2 students

Project Length

10 weeks


Applications open on 01/03/2020 and close on 02/05/2020


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If you have questions, please contact Karyn Belanger (kgbelanger@colgate.edu).