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

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 Agrobacte...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2019-01, Vol.17 (5), p.1090-1096
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
Subjects:
Affinity
Agrobacterium
Carbon sources
Crystallography
Glucose
Lactic acid
Life Sciences
NMR
Nuclear magnetic resonance
Phosphate esters
Phosphates
Phosphodiesterase
Proteins
Substrates
X-ray crystallography
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob03086c