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Molecules. 2017 Oct 10;22(10). pii: E1682. doi: 10.3390/molecules22101682.

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

Author information

1
Department of Chemistry, Rhodes College, 2000 North Parkway, Memphis, TN 38112, USA. snmalkowski@gmail.com.
2
Department of Chemistry, Rhodes College, 2000 North Parkway, Memphis, TN 38112, USA. cdishuck@gmail.com.
3
Department of Chemistry, Rhodes College, 2000 North Parkway, Memphis, TN 38112, USA. gene.lamanilao@gmail.com.
4
Department of Chemistry, Rhodes College, 2000 North Parkway, Memphis, TN 38112, USA. embcp-19@rhodes.edu.
5
Department of Chemistry, Rhodes College, 2000 North Parkway, Memphis, TN 38112, USA. csg2140@cumc.columbia.edu.
6
Department of Chemistry, Rhodes College, 2000 North Parkway, Memphis, TN 38112, USA. cafierom@rhodes.edu.
7
Department of Chemistry, Rhodes College, 2000 North Parkway, Memphis, TN 38112, USA. petersonl@rhodes.edu.

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.

KEYWORDS:

1,2,3-triazole; CuAAC; LpxC; antibacterial; click chemistry; nucleoside

PMID:
28994722
DOI:
10.3390/molecules22101682
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