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Synthesis of N-Acetylneuraminic acid derivatives, focusing on olefination reaction on C-7

Lund, Hannah LU (2023) KEML10 20231
Department of Chemistry
Abstract
The threat of resistant bacteria is an increasing issue that has emphasized the need for therapeutic strategies. One possible drug candidate is the carbohydrate sialic acid, which adorns almost every cell surface on mammalian cells. These so-called glycans (defined as carbohydrate-based polysaccharides) are involved in key cell functions, including cell-to-cell recognition in eukaryotes. Because of their importance in a cell’s overall health, irregularities may lead to human disease. For example, bacteria have developed the skill to import sialic acid onto their surface glycoconjugates which mask them from getting spotted by the human immune defense.
This project aims to create a molecular library of sialic acid derivatives, that could... (More)
The threat of resistant bacteria is an increasing issue that has emphasized the need for therapeutic strategies. One possible drug candidate is the carbohydrate sialic acid, which adorns almost every cell surface on mammalian cells. These so-called glycans (defined as carbohydrate-based polysaccharides) are involved in key cell functions, including cell-to-cell recognition in eukaryotes. Because of their importance in a cell’s overall health, irregularities may lead to human disease. For example, bacteria have developed the skill to import sialic acid onto their surface glycoconjugates which mask them from getting spotted by the human immune defense.
This project aims to create a molecular library of sialic acid derivatives, that could potentially disrupt bacteria’s ability to perform masking. The strategy used is to synthesize sialic acid derivatives by modifying position 7 in the molecule.
A powerful precursor that could potentially be used for the metathesis reaction was generated in the project. Furthermore, a methodology in which alkenes can be introduced at C-7 was optimized. (Less)
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author
Lund, Hannah LU
supervisor
organization
course
KEML10 20231
year
type
M2 - Bachelor Degree
subject
keywords
molecular library, biochemistry, sialic acid
language
English
id
9124198
date added to LUP
2023-07-14 10:40:46
date last changed
2023-07-14 10:40:46
@misc{9124198,
  abstract     = {{The threat of resistant bacteria is an increasing issue that has emphasized the need for therapeutic strategies. One possible drug candidate is the carbohydrate sialic acid, which adorns almost every cell surface on mammalian cells. These so-called glycans (defined as carbohydrate-based polysaccharides) are involved in key cell functions, including cell-to-cell recognition in eukaryotes. Because of their importance in a cell’s overall health, irregularities may lead to human disease. For example, bacteria have developed the skill to import sialic acid onto their surface glycoconjugates which mask them from getting spotted by the human immune defense. 
This project aims to create a molecular library of sialic acid derivatives, that could potentially disrupt bacteria’s ability to perform masking. The strategy used is to synthesize sialic acid derivatives by modifying position 7 in the molecule.
A powerful precursor that could potentially be used for the metathesis reaction was generated in the project. Furthermore, a methodology in which alkenes can be introduced at C-7 was optimized.}},
  author       = {{Lund, Hannah}},
  language     = {{eng}},
  note         = {{Student Paper}},
  title        = {{Synthesis of N-Acetylneuraminic acid derivatives, focusing on olefination reaction on C-7}},
  year         = {{2023}},
}