Towards the synthesis of poly(L-glutamine) study of the deprotection of poly(benzyl-L-glutamate)
Date of Award
Master of Science (MS)
Glutamine, Amino acids--Analysis, Huntington's disease
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.
Sentell, Andrew, "Towards the synthesis of poly(L-glutamine) study of the deprotection of poly(benzyl-L-glutamate)" (2023). Theses. 450.