Towards the synthesis of poly(L-glutamine) study of the deprotection of poly(benzyl-L-glutamate)

Author

Andrew Sentell

Date of Award

2023

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

Committee Chair

Carmen Scholz

Committee Member

Pamela Twigg

Committee Member

Jie Ling

Subject(s)

Glutamine, Amino acids--Analysis, Huntington's disease

Abstract

Polyglutamine segments of higher chain lengths are at the core of Huntington’s disease. The synthesis of poly(L-glutamine), including the deprotection and polymer analogous conversion of poly(L-glutamate) were investigated. First, the synthesis of hex-poly(benzyl-L-glutamate) was investigated and analyzed through ¹H NMR techniques. This research concentrated on the conversion from hex-poly(benzyl-L-glutamate) to hex-poly(L-glutamic acid) through deprotection of its benzyl functional group by the following deprotection methods: trimethylsilyl iodide (TMSI), NaOH, K₂CO₃, and HBr/CH₃COOH. The resulting polymers were characterized by ¹H NMR spectroscopy, and the TMSI, NaOH, and HBr/ CH₃COOH deprotection methods were most successful. The results indicate that NaOH deprotection is the most consistent and efficient deprotection. Next, the conversion from hex-poly(L-glutamic acid) to hex-poly(L-glutamine) through EDC/NHS coupling and subsequent treatment with NH₃/THF was investigated.

Recommended Citation

Sentell, Andrew, "Towards the synthesis of poly(L-glutamine) study of the deprotection of poly(benzyl-L-glutamate)" (2023). Theses. 450.
https://louis.uah.edu/uah-theses/450