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https://zone.biblio.laurentian.ca/handle/10219/2699
Title: | The synthesis of macrocyclic molecules related to telomestatin |
Authors: | Aldarini, Wafa Saeed S. |
Keywords: | G-quadruplexes;telomestatin;poly-oxazole macrocycles;macrocyclization;dinuclear copper (II) complex |
Issue Date: | 13-Jan-2017 |
Abstract: | G-quadruplex DNA represents an attractive target for the development of anti-cancer therapeutic agents as it plays important roles in transcriptional regulation and the maintenance of telomeric length. Oxazole-containing macrocycles such as telomestatin are considered to be a promissing new class of G-quadruplex binding ligands. In this work, poly-oxazole building blocks were synthesized to prepare a tetraoxazole peptide macrocycle in good yield. The macrocycle was obtained by employing standard peptide coupling conditions using a convergent solution phase approach. The synthetic unit of the oxazole amino acid containing compound was prepared by cyclodehydration/oxidation of protected serine and phenylalanine. Two-cycle coupling of the unit gave a linear tetraoxazole amide. The final macrocyclization was accomplished by using O-[(1-cyano-2-ethoxy-2-oxoethylidene)amino]-oxytri(pyrrolidin-1-yl) phosphonium hexafluorophosphate (PyOxP) and the product (45% yield) was characterized by 1H NMR. Finally, the Cu (II) coordination chemistry of the tetraoxazole macrocycle was investigated by spectrophotometric titration. |
URI: | https://zone.biblio.laurentian.ca/handle/10219/2699 |
Appears in Collections: | Chemical Sciences - Master's Theses Master's Theses |
Files in This Item:
File | Description | Size | Format | |
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Wafa Aldarini MSc thesis final.pdf | 5.62 MB | Adobe PDF | View/Open |
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