Synthesis of a non-natural glucose-2-phosphate ester able to dupe the acc system of Agrobacterium fabrum

Si-Zhe Li (1) , Armelle Vigouroux (2, 3) , Mohammed Ahmar (1) , Abbas El Sahili (2, 3) , Laurent Soulere (1) , Laila Sago (4, 2) , David Cornu (2, 4) , Solange Moréra (2, 3) , Yves Queneau (1)

1 COB - Chimie Organique et Bioorganique
2 I2BC - Institut de Biologie Intégrative de la Cellule
3 MESB3S - Microbiologie et enzymologie structurale
4 SICaPS - SICaPS

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 tumefa-ciens). 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, enzy-matic 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.

Mots clés: phosphate; opines; hydrolysis; diesters; plasmids; glycogen

Domaines: Sciences du Vivant [q-bio]

Si-Zhe Li, Armelle Vigouroux, Mohammed Ahmar, Abbas El Sahili, Laurent Soulere, et al.. Synthesis of a non-natural glucose-2-phosphate ester able to dupe the acc system of Agrobacterium fabrum. Organic & Biomolecular Chemistry, 2019, 17 (5), pp.1090--1096. ⟨10.1039/c8ob03086c⟩. ⟨hal-02173130⟩