Abstract
Agrocin 108 is a 3′-O-β-D-xylopyranosyl-cytidine-5′-O-phosphodiester of an ascorbate-carbocyclic cyclopentenone analogue, with bacteriocin-like properties. This bacteriocin exhibits orders of magnitude greater than the inhibition zone diameter towards the indicator strain than either ampicillin or streptomycin. It has been isolated from cultures of Rhizobium rhizogenes strain K108. The structure of the agrocin 108 without detail, has been previously published. We now report a detailed structure elucidation, including the hitherto undetermined residual 5′-phospho-diester fragment by a combination of 1D and 2D NMR studies at various pH values in H2O/D2O, high resolution MS, pKa determination, and chemical degradation.
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Acknowledgements
The authors thank Professor Allen Kerr for the bacterial strains and extensive discussions. Philip Clements is thanked for providing the 600 MHz NMR data and Mark Solomon for the high resolution electrospray mass spectrometry data. The former support of Australian Research Council and latter the University of Adelaide Alumni Association is gratefully acknowledged. This paper is dedicated to the memory of Max E. Tate (deceased 2016).
Author contributions
CE and the late MET performed the original 1979 investigation, intermittent studies by SD and the late MET culminated in 2016, when sufficient spectroscopic data were accumulated with the help of RA, for a rational complete structure. MR provided recent microbiological activity information and GPJ assisted in the interpretation of the NMR data. The late MET, RA, and GPJ prepared the manuscript.
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Elvin, C.M., Asenstorfer, R.E., Ryder, M.H. et al. Agrocin 108 is a 5'-cytidine nucleotide bacteriocin containing a carbocyclic phosphoryl-ascorbate group. J Antibiot 71, 438–446 (2018). https://doi.org/10.1038/s41429-017-0014-y
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DOI: https://doi.org/10.1038/s41429-017-0014-y
