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. 2020 Jun 19;25(12):2829.
doi: 10.3390/molecules25122829.

Esters of Glucose-2-Phosphate: Occurrence and Chemistry

Qiang Zhang  1 , Si-Zhe Li  1 , Mohammed Ahmar  1 , Laurent Soulère  1 , Yves Queneau  1
Affiliations

Esters of Glucose-2-Phosphate: Occurrence and Chemistry

Qiang Zhang et al. Molecules. .

Abstract

Phosphodiesters of glucose-2-phosphate (G2P) are found only in few natural compounds such as agrocinopine D and agrocin 84. Agrocinopine D is a G2P phosphodiester produced by plants infected by Agrobacterium fabrum C58 and recognized by the bacterial periplasmic binding protein AccA for being transported into the bacteria before cleavage by the phosphodiesterase AccF, releasing G2P, which promotes virulence by binding the repressor protein AccR. The G2P amide agrocin 84 is a natural antibiotic produced by the non-pathogenic Agrobacterium radiobacter K84 strain used as a biocontrol agent by competing with Agrobacterium fabrum C58. G2P esters are also found in irregular glycogen structures. The rare glucopyranosyl-2-phophoryl moiety found in agrocin 84 is the key structural signature enabling its action as a natural antibiotic. Likewise, G2P and G2P esters can also dupe the Agrobacterium agrocinopine catabolism cascade. Such observations illustrate the importance of G2P esters on which we have recently focused our interest. After a brief review of the reported phosphorylation coupling methods and the choice of carbohydrate building blocks used in G2P chemistry, a flexible access to glucose-2-phosphate esters using the phosphoramidite route is proposed.

Keywords: Agrobacterium fabrum; agrocin 84; agrocinopine; glucose-2-phosphate; phosphodiesters.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structures of agrocinopines A, B, C and D, d-glucose-2-phosphate (G2P) and its esters G2P lactate, its amide agrocin 84.
Scheme 1
Scheme 1
Previous synthesis of the precursors of agrocinopine C and D, G2P and G2LP.
Scheme 2
Scheme 2
Previous synthetic routes for acetylated glucose with 2-OH free [21,22,23,24].
Scheme 3
Scheme 3
Various accesses to tetrabenzylated glucose with 2-OH free [26,27,28,29].
Scheme 4
Scheme 4
Synthesis of the precursor of agrocinopine D in one-pot.
Scheme 5
Scheme 5
Deprotection of the phosphate precursors.
See this image and copyright information in PMC

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