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Synthesis and activity of 5'-uridinyl dipeptide analogues mimicking the amino terminal peptide chain of nucleoside antibiotic mureidomycin A
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UNSPECIFIED (2003) Synthesis and activity of 5'-uridinyl dipeptide analogues mimicking the amino terminal peptide chain of nucleoside antibiotic mureidomycin A. BIOORGANIC & MEDICINAL CHEMISTRY, 11 (14). pp. 3083-3099. doi:10.1016/S0968-0896(03)00207-0 ISSN 0968-0896.
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Official URL: http://dx.doi.org/10.1016/S0968-0896(03)00207-0
Abstract
A series of 5'-uridinyl dipeptides were synthesised which mimic the amino terminal chain of nucleoside antibiotic mureido omycin A. Aminoacyl-beta-alanyl- and aminoacyl-N-methyl-beta-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 phosphoMurNAc-pentapeptide translocase (MraY) was 5'-O-((L)-Ala-N-methyl-beta-alanyl)-uridine (131), which also showed 97% enzyme inhibition at 2.35mM concentration, and showed antibacterial activity at 100 mug/mL concentration against Pseudomonas putida. Both the central N-methyl amide linkage and a 5' uridine ester linkage were required for highest biological activity. Enzyme inhibition was shown to be competitive with Mg2+. It is proposed that the primary amino terminus of the inhibitor binds in place of the Mg2+. cofactor at the MraY active site, positioned via a cis-N-methyl amide linkage. (C) 2003 Elsevier Science Ltd. All rights reserved.
Item Type: | Journal Article | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Journal or Publication Title: | BIOORGANIC & MEDICINAL CHEMISTRY | ||||
Publisher: | PERGAMON-ELSEVIER SCIENCE LTD | ||||
ISSN: | 0968-0896 | ||||
Official Date: | 17 July 2003 | ||||
Dates: |
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Volume: | 11 | ||||
Number: | 14 | ||||
Number of Pages: | 17 | ||||
Page Range: | pp. 3083-3099 | ||||
DOI: | 10.1016/S0968-0896(03)00207-0 | ||||
Publication Status: | Published |
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