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Chemical structure and translation inhibition studies of the antibiotic microcin C7.

Abstract : Escherichia coli microcin C7 (MccC7) is an antibiotic that inhibits protein synthesis in vivo. It is a heptapeptide containing unknown modifications at the N and C termini (Garc?Bustos, J. F., Pezzi, N., and M?ez, E. (1985) Antimicrob. Agents Chemoth. 27, 791-797). The chemical structure of MccC7 has been characterized by use of 1H homonuclear and heteronuclear (13C, 15N, 31P) nuclear magnetic resonance spectroscopy as well as mass spectrometry (1177 +/- 1 Da). The heptapeptide Met-Arg-Thr-Gly-Asn-Ala-Asp is substituted at the N terminus by a N-formyl group. The C-terminal substituent consists of the phosphodiester of 5'-adenylic acid and n-aminopropanol (AMPap), which is linked via the phosphorus atom to an amide group, thus forming a phosphoramide. The main chain carbonyl of the C-terminal aspartic acid residue is connected via this amide bond to the modified nucleotide unit. MccC7 and the peptide unit inhibit protein translation in vitro while a synthetic analog of the AMPap substituent is not active. Neither the peptide nor the AMPap molecule has an effect on the growth of MccC7-sensible cells. Our results strongly suggest that the peptide is responsible for MccC7 antibiotic activity while the C-terminal substituent is needed for MccC7 transport. Implications of the structure determined in this work for MccC7 synthesis and mode of action are discussed.
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Contributor : Cécile Roux Connect in order to contact the contributor
Submitted on : Friday, February 27, 2009 - 3:47:40 PM
Last modification on : Thursday, April 7, 2022 - 10:10:19 AM
Long-term archiving on: : Saturday, November 26, 2016 - 6:04:15 AM

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J. I. Guijarro, J. E. González-Pastor, F. Baleux, J. L. San Millán, M. A. Castilla, et al.. Chemical structure and translation inhibition studies of the antibiotic microcin C7.. Journal of Biological Chemistry, 1995, 270 (40), pp.23520-32. ⟨10.1074/jbc.270.40.23520⟩. ⟨pasteur-00364887⟩

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