Synthesis of novel C7-modified sialic acids
(2025) KEMP60 20251Department of Chemistry
- Abstract
- Sialic acids are a group of 9-carbon carbohydrates abundant in humans, where they can be found on the surface of all cell types. They play an important role in biological signaling and therefore numerous physiological and pathophysiological processes. Some pathogenic bacteria are able to use the sialic acid of its host, which they uptake through transporters in their membrane, as an energy source as well as a method for immunoevasion through molecular mimickry. One potential method for the prevention and treatment of infections with such bacteria is the inhibition of the bacterial sialic acid transporter by modified sialic acids with high affinity to the transporter. This project focused on modifications on the C7-position of sialic acids,... (More)
- Sialic acids are a group of 9-carbon carbohydrates abundant in humans, where they can be found on the surface of all cell types. They play an important role in biological signaling and therefore numerous physiological and pathophysiological processes. Some pathogenic bacteria are able to use the sialic acid of its host, which they uptake through transporters in their membrane, as an energy source as well as a method for immunoevasion through molecular mimickry. One potential method for the prevention and treatment of infections with such bacteria is the inhibition of the bacterial sialic acid transporter by modified sialic acids with high affinity to the transporter. This project focused on modifications on the C7-position of sialic acids, of which not much is yet known. Therefore, a library of compounds was to be obtained for screening studies of their affinity to the sialic acid transporter. Several novel compounds were obtained, however no screening studies could be done, since significant issues with the deprotection of a protecting group of the anomeric position arose. One novel method for deprotection was found, which yielded a glycal of a modified sialic acid that might as well be of interest. (Less)
- Popular Abstract
- Sialic acids are a type of sugar that occurs the cells of humans. They are important for the communication of the cells with each other. Sialic acids play therefore an important role in many normal biological processes, but also in many diseases. Some bacteria which cause infections in humans are able to use the sialic acid as food for themselves; and as a method
to trick the human immune system into not recognizing the bacteria as a threat. One potential method for the prevention and treatment of such infections is to prevent the uptake of sialic acid in those bacteria. This can be achieved by using modified sialic acids which block the transport protein of the actual sialic acid. This project focused on modifications on the C7-position... (More) - Sialic acids are a type of sugar that occurs the cells of humans. They are important for the communication of the cells with each other. Sialic acids play therefore an important role in many normal biological processes, but also in many diseases. Some bacteria which cause infections in humans are able to use the sialic acid as food for themselves; and as a method
to trick the human immune system into not recognizing the bacteria as a threat. One potential method for the prevention and treatment of such infections is to prevent the uptake of sialic acid in those bacteria. This can be achieved by using modified sialic acids which block the transport protein of the actual sialic acid. This project focused on modifications on the C7-position of sialic acids, which is a position on the molecule of which not a lot is known yet. Therefore, it was the goal to make many different modified sialic acids and screen them for their ability to block the transport protein. Several novel modified compounds were obtained, however no screening studies could be done, since significant issues during the final steps of the synthesis arose. Thereby, a different modified version of sialic acid was yielded, that might as well be of biological interest. (Less)
Please use this url to cite or link to this publication:
http://lup.lub.lu.se/student-papers/record/9188146
- author
- Gleichauf, Luisa LU
- supervisor
- organization
- course
- KEMP60 20251
- year
- 2025
- type
- L3 - Miscellaneous, Projetcs etc.
- subject
- keywords
- organic chemistry
- language
- English
- id
- 9188146
- date added to LUP
- 2025-05-09 10:17:24
- date last changed
- 2025-05-09 10:17:24
@misc{9188146,
abstract = {{Sialic acids are a group of 9-carbon carbohydrates abundant in humans, where they can be found on the surface of all cell types. They play an important role in biological signaling and therefore numerous physiological and pathophysiological processes. Some pathogenic bacteria are able to use the sialic acid of its host, which they uptake through transporters in their membrane, as an energy source as well as a method for immunoevasion through molecular mimickry. One potential method for the prevention and treatment of infections with such bacteria is the inhibition of the bacterial sialic acid transporter by modified sialic acids with high affinity to the transporter. This project focused on modifications on the C7-position of sialic acids, of which not much is yet known. Therefore, a library of compounds was to be obtained for screening studies of their affinity to the sialic acid transporter. Several novel compounds were obtained, however no screening studies could be done, since significant issues with the deprotection of a protecting group of the anomeric position arose. One novel method for deprotection was found, which yielded a glycal of a modified sialic acid that might as well be of interest.}},
author = {{Gleichauf, Luisa}},
language = {{eng}},
note = {{Student Paper}},
title = {{Synthesis of novel C7-modified sialic acids}},
year = {{2025}},
}