1011723-04-8Relevant articles and documents
Esters of Glucose-2-Phosphate: Occurrence and Chemistry
Ahmar, Mohammed,Li, Si-Zhe,Queneau, Yves,Soulère, Laurent,Zhang, Qiang
, (2020)
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.
Light-Mediated Cross-Coupling of Anomeric Trifluoroborates
Miller, Eric M.,Walczak, Maciej A.
, p. 4289 - 4293 (2021)
Stereoselective reactions at the anomeric carbon constitute the cornerstone of preparative carbohydrate chemistry. Here, we report stereoselective C-arylation and etherification reactions of anomeric trifluoroborates derived from BMIDA esters. These react
Highly Stereospecific Cross-Coupling Reactions of Anomeric Stannanes for the Synthesis of C-Aryl Glycosides
Zhu, Feng,Rourke, Michael J.,Yang, Tianyi,Rodriguez, Jacob,Walczak, Maciej A.
, p. 12049 - 12052 (2016/10/03)
We demonstrate that configurationally stable anomeric stannanes undergo a stereospecific cross-coupling reaction with aromatic halides in the presence of a palladium catalyst with exceptionally high levels of stereocontrol. In addition to a broad substrat
Synthesis of water soluble O-glycosides of N-(hydroxyalkyl)-aminomethylferrocenes
Landells, John S.,Kerr, Joy L.,Larsen, David S.,Robinson, Brian H.,Simpson, Jim
, p. 1403 - 1409 (2007/10/03)
A series of water soluble ferrocenylamine-glucose conjugates, [N-2-(p-D-glucopyranosyloxy)ethyl-, [N-3-(β-D-glucopyranosyloxy)propyl-, [B-5-(β-D-glucopyranosyloxy)pentyl-N-methylaminomethyl]ferrocene, has been synthesized from the methiodide salt of ./V.TV-dimethylaminomethylferrocene and N-(S.o-tri-O-benzyl-β-Dglucopyranosyloxy-ethyl, -propyl and -pentyl)amine respectively. W-Methylation of the products from the latter reaction was achieved by formylation followed by reduction with lithium aluminium hydride. Catalytic hydrogenolysis over palladium removed the benzyl protecting groups from the carbohydrate moiety to give the target conjugates. An alternative synthesis of [N-2-(β-D-glucopyranosyloxyethyl)aminomethyl]ferrocene using boron trifluoride-diethyl ether promoted glycosylation of penta-0-acetyl-D-glucopyranose and [A-(2-hydroxyethyl)N-methylaminomethyl]ferrocene followed by deacetylation of the carbohydrate protecting group using basic ion exchange resin was also developed. The pK, values of the water soluble conjugates were determined. The Royal Society of Chemistry 2000.
