Efficient synthesis of triazole moiety-containing nucleotide analogs and their inhibitory effects on a malic enzyme

Shuhua Hou; Wujun Liu; Debin Ji; Zongbao Kent Zhao

doi:10.1016/j.bmcl.2011.01.107

Efficient synthesis of triazole moiety-containing nucleotide analogs and their inhibitory effects on a malic enzyme

Bioorg Med Chem Lett. 2011 Mar 15;21(6):1667-9. doi: 10.1016/j.bmcl.2011.01.107. Epub 2011 Jan 27.

Authors

Shuhua Hou¹, Wujun Liu, Debin Ji, Zongbao Kent Zhao

Affiliation

¹ Dalian Institute of Chemical Physics, CAS, Dalian, PR China.

PMID: 21324682
DOI: 10.1016/j.bmcl.2011.01.107

Abstract

Eleven triazole moiety-containing nucleotide analogs were synthesized starting form tetra-O-acetylribose in 55-63% total yields. The synthesis involved two key steps, the lipase-mediated selective deacylation of 1-azido-2,3,5-tri-O-acetyl-β-D-ribofuranoside and the Huisgen 1,3-dipolar cycloaddition between terminal alkynes and the 1-azido ribofuranoside derivative. These analogs showed inhibitory effects against a recombinant Escherichia coli NAD-dependent malic enzyme.

MeSH terms

Enzyme Inhibitors / chemical synthesis*
Escherichia coli / drug effects
Malate Dehydrogenase / antagonists & inhibitors*
Nucleotides / chemical synthesis*
Triazoles / chemistry*

Substances

Enzyme Inhibitors
Nucleotides
Triazoles
Malate Dehydrogenase
malate dehydrogenase-(oxaloacetate-decarboxylating) (NAD+)