Synthesis of a non-natural glucose-2-phosphate ester able to dupe the acc system of Agrobacterium fabrumElectronic supplementary information (ESI) available: NMR spectra for new compounds, 2D NMR structural elucidation of G2LP and crystallographic data and refinement parameters for the structure of AccA in complex with G2LP. See DOI: 10.1039/c8ob03086c

• Main Authors: Li, Si-Zhe, Vigouroux, Armelle, Ahmar, Mohammed, El Sahili, Abbas, Soulère, Laurent, Sago, Laïla, Cornu, David, Moréra, Solange, Queneau, Yves
• Format: Article
• Language: English
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/c8ob03086c

The first non-natural derivative of the rare d -glucose-2-phosphate (G2P), namely glucose-2-( O -lactic acid phosphate) (G2LP), has been synthesized. When used as sole carbon source, G2LP enables bacterial growth of the plant pathogenic strain Agrobacterium fabrum C58 (formerly referred to as Agrobacterium tumefaciens ). X-ray crystallography and affinity measurements investigations reveal that G2LP binds the periplasmic binding protein (PBP) AccA similarly to the natural compounds and with the same affinity. Moreover, enzymatic assays show that it is able to serve as substrate of the phosphodiesterase AccF. The properties found for G2LP demonstrate that the very unusual glucose-2-phosphoryl residue, present in G2LP, can be used as structural feature for designing non-natural systems fully compatible with the Acc cascade of A. fabrum . Novel non-natural G2P ester G2LP can enter A. fabrum and serve as nutrient. Binding to AccA and activity vs. AccF is fully demonstrated.