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Mimicking Sialic Acid: Design and Synthesis of Bacterial Uptake Blockers

Alsalehe, Ahmed Aadl LU (2025) KEMR45 20251
Department of Chemistry
Abstract
Antimicrobial resistance (AMR) is a growing global health concern, driven by the overuse of
antibiotics and a lack of new drug development. To address this challenge, alternative
antibacterial targets involved in essential bacterial functions are being explored.
In this study, three compounds were synthesized using N-acetylglucosamine as the starting
material. One of these compounds serves as a key intermediate for further derivatization via
nucleophilic substitution reactions, owing to the presence of a reactive bromide leaving group
that can be readily replaced by various nucleophiles. The structures and purity of the
synthesized compounds were confirmed. Furthermore, theoretical interactions between these
compounds and membrane... (More)
Antimicrobial resistance (AMR) is a growing global health concern, driven by the overuse of
antibiotics and a lack of new drug development. To address this challenge, alternative
antibacterial targets involved in essential bacterial functions are being explored.
In this study, three compounds were synthesized using N-acetylglucosamine as the starting
material. One of these compounds serves as a key intermediate for further derivatization via
nucleophilic substitution reactions, owing to the presence of a reactive bromide leaving group
that can be readily replaced by various nucleophiles. The structures and purity of the
synthesized compounds were confirmed. Furthermore, theoretical interactions between these
compounds and membrane proteins were investigated to evaluate their potential as
antibacterial agents. (Less)
Popular Abstract
Antibiotic resistance is becoming one of the greatest health threats of our time. Bacteria that were once easily treated with antibiotics are now developing resistance, making infections harder—and sometimes impossible—to cure. This problem is compounded by the fact that, although a few new antibiotics have reached clinical use, the development of truly novel antibiotic classes has been extremely limited in recent decades. As we search for new ways to fight bacteria, scientists are looking beyond traditional antibiotics and exploring different strategies to disarm bacteria and prevent infections.
One such strategy involves targeting sialic acid, a sugar molecule found on the surface of human cells. Sialic acids play important roles in... (More)
Antibiotic resistance is becoming one of the greatest health threats of our time. Bacteria that were once easily treated with antibiotics are now developing resistance, making infections harder—and sometimes impossible—to cure. This problem is compounded by the fact that, although a few new antibiotics have reached clinical use, the development of truly novel antibiotic classes has been extremely limited in recent decades. As we search for new ways to fight bacteria, scientists are looking beyond traditional antibiotics and exploring different strategies to disarm bacteria and prevent infections.
One such strategy involves targeting sialic acid, a sugar molecule found on the surface of human cells. Sialic acids play important roles in health and disease and are used by some bacteria in clever ways to survive. Interestingly, while humans can produce sialic acids naturally, most bacteria cannot. Instead, they steal these sugars from their host. Once inside the bacterial cell, sialic acids can either be used as food or be added to the bacterial surface to make them look like human cells. This camouflage, called molecular mimicry, helps bacteria hide from the immune system and establish infections.
Scientists have discovered that if we block the bacteria's ability to take up sialic acid, they lose this protective camouflage and become more vulnerable to the immune system. This approach is especially exciting because the way humans and bacteria handle sialic acid is very different, meaning that drugs targeting this process in bacteria are unlikely to harm human cells. Early research has shown that disrupting sialic acid uptake in bacteria like Haemophilus influenzae can reduce their ability to resist immune attacks. This makes the bacterial sialic acid transport systems a promising new target in the fight against antibiotic-resistant infections. (Less)
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author
Alsalehe, Ahmed Aadl LU
supervisor
organization
course
KEMR45 20251
year
type
H2 - Master's Degree (Two Years)
subject
keywords
Organic chemistry, Mimicking Sialic Acid, Sialic Acid, N-acetylglucosamine, Bacterial Uptake Blockers, Antibiotics, Neu5Gc, Neu5Ac
language
English
id
9191433
date added to LUP
2025-06-05 13:23:48
date last changed
2025-06-05 13:23:48
@misc{9191433,
  abstract     = {{Antimicrobial resistance (AMR) is a growing global health concern, driven by the overuse of
antibiotics and a lack of new drug development. To address this challenge, alternative
antibacterial targets involved in essential bacterial functions are being explored.
In this study, three compounds were synthesized using N-acetylglucosamine as the starting
material. One of these compounds serves as a key intermediate for further derivatization via
nucleophilic substitution reactions, owing to the presence of a reactive bromide leaving group
that can be readily replaced by various nucleophiles. The structures and purity of the
synthesized compounds were confirmed. Furthermore, theoretical interactions between these
compounds and membrane proteins were investigated to evaluate their potential as
antibacterial agents.}},
  author       = {{Alsalehe, Ahmed Aadl}},
  language     = {{eng}},
  note         = {{Student Paper}},
  title        = {{Mimicking Sialic Acid: Design and Synthesis of Bacterial Uptake Blockers}},
  year         = {{2025}},
}