Design and synthesis of a bifunctional linker for N-linked glycopeptide synthesis
N-linked glycopeptides and cyclic peptide are an important class of compounds. Many of these naturally occurring compounds possess therapeutic value which could be used for treating antimicrobial resistance infections. However, these compounds were under-utilized for drug discovery as it is difficul...
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sg-ntu-dr.10356-1611922023-02-28T23:44:06Z Design and synthesis of a bifunctional linker for N-linked glycopeptide synthesis Lin, Desmond Junjie Liu Xuewei School of Physical and Mathematical Sciences XueWei@ntu.edu.sg Science::Chemistry::Organic chemistry N-linked glycopeptides and cyclic peptide are an important class of compounds. Many of these naturally occurring compounds possess therapeutic value which could be used for treating antimicrobial resistance infections. However, these compounds were under-utilized for drug discovery as it is difficult to purify them from natural product and synthesis of these compounds in large quantity is laborious. Throughout the last few decades, there has been an increasing number of reports on total synthesis of these compounds with biological significance and novel methodology for synthesizing these valuable compounds at ease. Recognizing the significance of these compounds, thus, the aim of my thesis is to contribute to this field of research by expanding the toolbox for peptide ligation with new methodology. This thesis starts off with an overview of novel methodologies which have been utilized in peptide ligation and synthesis of glycopeptide in the past few decades. In the next chapter, it describes my work in designing and synthesis of a bifunctional linker that could facilitate the synthesis of N-glycopeptide through native chemical ligation and “traceless” Staudinger ligation. The reaction process resembles sugar assisted ligation and dual native chemical ligation with the exception that no additional auxiliary removal step is required after the ligations. Lastly, this thesis will end with third chapter exploring and discussing on macrocyclization of peptide with our designed linker via two potential pathways, namely, native chemical ligation based macrocyclization and “traceless” Staudinger ligation based macrocyclization. Doctor of Philosophy 2022-08-19T01:17:48Z 2022-08-19T01:17:48Z 2022 Thesis-Doctor of Philosophy Lin, D. J. (2022). Design and synthesis of a bifunctional linker for N-linked glycopeptide synthesis. Doctoral thesis, Nanyang Technological University, Singapore. https://hdl.handle.net/10356/161192 https://hdl.handle.net/10356/161192 10.32657/10356/161192 en This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License (CC BY-NC 4.0). application/pdf Nanyang Technological University |
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Science::Chemistry::Organic chemistry Lin, Desmond Junjie Design and synthesis of a bifunctional linker for N-linked glycopeptide synthesis |
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N-linked glycopeptides and cyclic peptide are an important class of compounds. Many of these naturally occurring compounds possess therapeutic value which could be used for treating antimicrobial resistance infections. However, these compounds were under-utilized for drug discovery as it is difficult to purify them from natural product and synthesis of these compounds in large quantity is laborious. Throughout the last few decades, there has been an increasing number of reports on total synthesis of these compounds with biological significance and novel methodology for synthesizing these valuable compounds at ease. Recognizing the significance of these compounds, thus, the aim of my thesis is to contribute to this field of research by expanding the toolbox for peptide ligation with new methodology.
This thesis starts off with an overview of novel methodologies which have been utilized in peptide ligation and synthesis of glycopeptide in the past few decades. In the next chapter, it describes my work in designing and synthesis of a bifunctional linker that could facilitate the synthesis of N-glycopeptide through native chemical ligation and “traceless” Staudinger ligation. The reaction process resembles sugar assisted ligation and dual native chemical ligation with the exception that no additional auxiliary removal step is required after the ligations. Lastly, this thesis will end with third chapter exploring and discussing on macrocyclization of peptide with our designed linker via two potential pathways, namely, native chemical ligation based macrocyclization and “traceless” Staudinger ligation based macrocyclization. |
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Liu Xuewei |
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Liu Xuewei Lin, Desmond Junjie |
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Thesis-Doctor of Philosophy |
author |
Lin, Desmond Junjie |
author_sort |
Lin, Desmond Junjie |
title |
Design and synthesis of a bifunctional linker for N-linked glycopeptide synthesis |
title_short |
Design and synthesis of a bifunctional linker for N-linked glycopeptide synthesis |
title_full |
Design and synthesis of a bifunctional linker for N-linked glycopeptide synthesis |
title_fullStr |
Design and synthesis of a bifunctional linker for N-linked glycopeptide synthesis |
title_full_unstemmed |
Design and synthesis of a bifunctional linker for N-linked glycopeptide synthesis |
title_sort |
design and synthesis of a bifunctional linker for n-linked glycopeptide synthesis |
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Nanyang Technological University |
publishDate |
2022 |
url |
https://hdl.handle.net/10356/161192 |
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