Bioorganic & medicinal chemistry

Synthesis and activity of 5′-uridinyl dipeptide analogues mimicking the amino terminal peptide chain of nucleoside antibiotic mureidomycin A

NI Howard, TDH Bugg

Index: Howard, Nigel I.; Bugg, Timothy D. H. Bioorganic and Medicinal Chemistry, 2003 , vol. 11, # 14 p. 3083 - 3099

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Citation Number: 48

Abstract

A series of 5′-uridinyl dipeptides were synthesised which mimic the amino terminal chain of nucleoside antibiotic mureido omycin A. Aminoacyl-β-alanyl-and aminoacyl-N-methyl-β- alanyl-dipeptides were attached either via an ester linkage to the 5′-hydroxyl of uridine, or via an amide linkage to 5′-amino-5′-deoxyuridine. The most active inhibitor of Escherichia coli phospho-MurNAc-pentapeptide translocase (MraY) was 5′-O-(l-Ala-N- ...