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

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Abstract

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.

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

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Publication details

The article was received on 12 Dec 2018, accepted on 04 Jan 2019 and first published on 04 Jan 2019


Article type: Paper
DOI: 10.1039/C8OB03086C
Citation: Org. Biomol. Chem., 2019, Advance Article
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    Synthesis of a non-natural glucose-2-phosphate ester able to dupe the acc system of Agrobacterium fabrum

    S. Li, A. Vigouroux, M. Ahmar, A. El Sahili, L. Soulère, L. Sago, D. Cornu, S. Moréra and Y. Queneau, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C8OB03086C

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