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Derivatives of N-acetylglucosamine-1-phosphate as potential inhibitors of UDP-GlcNAc pyrophosphorylase
Černá, Lucie ; Baszczyňski, Ondřej (advisor) ; Veselý, Jan (referee)
This bachelor thesis deals with the preparation of phosphonate derivatives of N-acetyl- ᴅ-glucosamine-1-phosphate (GlcNAc-1-P), the substrate for UDP-GlcNAc pyrophospho- rylase (UAP1) enzyme, which is responsible for the chitin synthesis in fungal cell walls. Structural analogs of GlcNAc-1-P could potentially inhibit UAP1 and; therefore, their synthesis may enable the development of new antifungal drugs. This work is mainly focused on the synthesis of diethyl (2-acetamido-1,2-dideoxy-β-ᴅ-glucopyranosyl)phosphonate which was selected as a key model compound. The goal was to find the most suitable synthetic route leading to the synthesis of phosphonate and phosphinate GlcNAc-1-P analogues. Two synthetic methods were studied: 1) Michael addition of H-phosphonates to 2-nitroglucals; and 2) nucleophilic substitution of activated GlcNAc substrates (trichloroacetimidate and bromide) by phosphorus nucleophiles. Keywords: GlcNAc-1-P, UDP-GlcNAc pyrophosphorylase, antifungal, inhibitor

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