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Microwave Assisted Glycosylation Under Neutral Conditions and Glyco-MUC1 based Cancer Vaccine

Gamage, Shanika Madhushani Perera
http://rave.ohiolink.edu/etdc/view?acc_num=toledo1689942707098628

Abstract Details

2023, Doctor of Philosophy, University of Toledo, Chemistry.
Neutral glycosylation, using microwave irradiation, is novel in the realm of carbohydrate chemistry. Providing mild reaction conditions, decreased reaction times and enabling good yields with high purity are the major advantages of microwave promoted reactions. Microwave assisted glycosylation is a rapidly emerging method in the field of carbohydrate chemistry. However only very few reports have described microwave assisted glycosylation. We have developed a microwave labile protecting group (MWLPG) which is selectively removed when microwave irradiation is applied, and it is orthogonal to other commonly used protecting groups. A dinitrophenyl (DNP) ring, at the anomeric position, gave good yields and high alpha selectivity with simple to complex glycosyl acceptors. The glycoside of DNP is labile to nucleophiles such as ammonia in methanol, but it is not reactive enough to undergo conventional glycosylation. However, the DNP donor is highly reactive under microwave heating with neutral to slightly basic conditions. In contrast to conventional glycosylation, this can be achieved without the use of chemical promoters, usually consisting of Lewis or Bronsted acids. Thermal activation of highly electron withdrawing sugar donors in the presence of microwave irradiation and in the absence of any external additives, albeit for the partnering acceptor and solvent to dissolve the coupling partners. DMF proved to be the best solvent for the reaction which is polar aprotic solvent with high dielectric constant. DNP donors decorated with electron-donating benzyl ethers showed increased reactivity in comparison to the DNP donors protected with electron-withdrawing acetate and benzoyl protecting groups, which are inert under microwave conditions. We have established a fast, high temperature glycosylation method by employing precise microwave heating.
Peter Andreana (Advisor)
258 p.
Chemistry
Carbohydrate Chemistry, Microwave heating, Neutral Glycosylation, MUC1, Cancer vaccines

Recommended Citations

Citations

  • Gamage, S. M. P. (2023). Microwave Assisted Glycosylation Under Neutral Conditions and Glyco-MUC1 based Cancer Vaccine [Doctoral dissertation, University of Toledo]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=toledo1689942707098628

    APA Style (7th edition)

  • Gamage, Shanika. Microwave Assisted Glycosylation Under Neutral Conditions and Glyco-MUC1 based Cancer Vaccine. 2023. University of Toledo, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=toledo1689942707098628.

    MLA Style (8th edition)

  • Gamage, Shanika. "Microwave Assisted Glycosylation Under Neutral Conditions and Glyco-MUC1 based Cancer Vaccine." Doctoral dissertation, University of Toledo, 2023. http://rave.ohiolink.edu/etdc/view?acc_num=toledo1689942707098628

    Chicago Manual of Style (17th edition)

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© 2023, all rights reserved.
This open access ETD is published by University of Toledo and OhioLINK.
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