Synthesis of Guaiazulene containing amino acid derivative using amino acid functionalized Fullerene derivatives

Date

2024-9-06

Author

Akar, Elif

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Fullerene C60, and its derivatives’ unique characteristics of easy chemical modification, conductivity, biocompatibility, and electrochemical properties enables them to participate in various chemical reactions as enzyme mimics or organocatalysts. In this study, different types of functional groups including sulfonic acid, carboxylic acid and guanidinium conjugated on fullerenol scaffolds were investigated as organocatalysts for the Michael addition reaction. In this context, 1,4-dimethyl-7- isopropylazulene (guaiazulene) was reacted with dehydroalanine derivative, Nphthaloyl dehydroalanine, via Michael-addition reaction. Fullerenol derivatives such as F-Glu and F-Arg was used to serve as hydrogen bond donors while F-Tau was used as acid catalyst in this reaction, suggesting that functional group on fullerenol scaffold activates carbonyl group on dehydroalanine which makes the conjugated double bond more susceptible for Michael-type addition of guaiazulene. Moreover, the Michael-addition product (N-Phth-Guaz-Ala-OH) was used to form noncanonical amino acid (Guaz-Ala-OH) and incorporated into the peptides as an analog of tryptophan. The abilities of Trp and guaiazulene to contribute selfassembly will be investigated by studying the gel formation of the peptides.

Subject Keywords

Fullerenes, Fullerene amino acid conjugates, Acid catalysts, Hydrogen-bond donor catalysts, Guaiazulene, Michael-addition reactions, Solid phase peptide synthesis

URI

https://hdl.handle.net/11511/111420

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Graduate School of Natural and Applied Sciences, Thesis