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

Molecules

Carter P. Embry¹  Larryn W. Peterson¹  Carolyn F. Dishuck¹  Gene G. Lamanilao¹  Christopher S. Grubb¹  Sarah N. Malkowski¹  Mauricio Cafiero¹ 

[1] Department of Chemistry, Rhodes College, 2000 North Parkway, Memphis, TN 38112, USA;

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

DOI  :  10.3390/molecules22101682

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown