Agrocin 108 is a 5'-cytidine nucleotide bacteriocin containing a carbocyclic phosphoryl-ascorbate group

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 H 2 O/D 2 O, high resolution MS, pKa determination, and chemical degradation.