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Molecules 2017, 22(10), 1682; doi:10.3390/molecules22101682

Design, Modeling and Synthesis of 1,2,3-Triazole-Linked Nucleoside-Amino Acid Conjugates as Potential Antibacterial Agents

Department of Chemistry, Rhodes College, 2000 North Parkway, Memphis, TN 38112, USA
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Received: 16 September 2017 / Revised: 27 September 2017 / Accepted: 3 October 2017 / Published: 10 October 2017
(This article belongs to the Section Bioorganic Chemistry)
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Abstract

Copper-catalyzed azide-alkyne cycloadditions (CuAAC or click chemistry) are convenient methods to easily couple various pharmacophores or bioactive molecules. A new series of 1,2,3-triazole-linked nucleoside-amino acid conjugates have been designed and synthesized in 57–76% yields using CuAAC. The azido group was introduced on the 5′-position of uridine or the acyclic analogue using the tosyl-azide exchange method and alkylated serine or proparylglycine was the alkyne. Modeling studies of the conjugates in the active site of LpxC indicate they have promise as antibacterial agents. View Full-Text
Keywords: click chemistry; CuAAC; 1,2,3-triazole; nucleoside; LpxC; antibacterial click chemistry; CuAAC; 1,2,3-triazole; nucleoside; LpxC; antibacterial
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Malkowski, S.N.; Dishuck, C.F.; Lamanilao, G.G.; Embry, C.P.; Grubb, C.S.; Cafiero, M.; Peterson, L.W. Design, Modeling and Synthesis of 1,2,3-Triazole-Linked Nucleoside-Amino Acid Conjugates as Potential Antibacterial Agents. Molecules 2017, 22, 1682.

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