659. Glucose-2 phosphate: its preparation and characterisation by hydrolysis studies

Three sugar phosphates, 4‐0‐(α‐D‐6‐phosphoglucosyl)‐D‐glucose, glucose 3‐phosphate, and glucose 6‐phosphate, were isolated from the α‐amylase limit phosphodextrin of potato starch by a partial acid hydrolysis and an ion exchange chromatography on Dowex‐1 × 8 formate resin. From the quantitative yields of glucose 3‐phosphate and glucose 6‐phosphate, the distribution of esterified phosphate in potato starch was estimated to be 38% on the C‐3, and 61% on the C‐6 of glucose residues. it was suggested from a kinetic study that approximately 1% of the phosphate in starch existed in a form more labile to acid than glucose 3‐phosphate, possibly as glucose 2‐phosphate.

show abstract

“…5). The value is a half of that of glc-2-P with 0.1 N H,SO, [16]. Therefore, Px, was more stable to acid than glc-2-P.…”

Section: Materials Totalmentioning

confidence: 89%

Studies on Starch Phosphate. Part 2. Isolation of Glucose 3‐Phosphate and Maltose Phosphate by Acid Hydrolysis of Potato Starch

1971

View full text Add to dashboard Cite

show abstract

“…Actually, glucose-2-phsophate itself was used for studying phosphate stability or hydrolysis rates [ 8 , 12 , 13 ], or for identification of the hydrolyzed monomeric forms of glycogen to understand the metabolism of the phosphate in this biopolymer [ 9 , 14 ]. The quite uncommon d -glucose-2-phosphate (G2P), which refer to phosphate covalently bonded glucose hydroxyl at C-2 position, was firstly and unequivocally synthesized by Farrar [ 15 ] in 1949. The hydrolysis of the cyclic glucose-1,2-phosphate (GCP) can afford a mixture of G2P and G1P.…”

Section: Resultsmentioning

confidence: 99%

“…The hydrolysis of the cyclic glucose-1,2-phosphate (GCP) can afford a mixture of G2P and G1P. During hydrolysis, G2P esters exhibit higher stability versus G1P [ 12 , 15 ].…”

Section: Resultsmentioning

confidence: 99%

“…Several methods have been developed in the field of carbohydrates and oligonucleotide [ 16 ], glycoside and peptide synthesis, but only few have been applied to the case of G2P and its esters. Farrar’s first unequivocal G2P synthesis [ 15 ] involved diphenyl chlorophosphate (3 days in pyridine) as phosphorylation reagent ( Scheme 1 ). The method used by Lindberg and Oscarson [ 17 ] for reaching an agrocinopine C precursor was the condensation of sucrose derivative and hydrogenphosphate in pyridine, while for reaching an agrocinopine D precursor, they performed the condensation of glucose derivative with a phosphonic acid in pyridine, activated by an acyl chloride [ 18 , 19 ].…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Esters of Glucose-2-Phosphate: Occurrence and Chemistry

Zhang

Ahmar

et al. 2020

Molecules

View full text Add to dashboard Cite

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.

show abstract

“…A few other G2P derivatives, namely the phosphodiester connecting two glucoses at O-2 and O-6, and a phenyl glucoside derivative were reported. [13][14][15] The quite rare D-glucose-2-phosphate, which we will refer to as G2P in this paper, is known since the late 1940's from the work by Fleury et al and by Farrar, 16,17 and has been observed as a product of the opening of the cyclic glucose-1,2-phosphate (GCP). 18 G2P was included in several studies on phosphate hydrolysis rates and phosphatases characterizations, 19 and used for analytical purposes for assessing starch or glycogen phosphorylation positions.…”

Section: Introductionmentioning

confidence: 99%

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

Vigouroux

Ahmar

et al. 2019

Org. Biomol. Chem.

View full text Add to dashboard Cite

show abstract

659. Glucose-2 phosphate: its preparation and characterisation by hydrolysis studies

Cited by 21 publications

References 0 publications

Studies on Starch Phosphate. Part 2. Isolation of Glucose 3‐Phosphate and Maltose Phosphate by Acid Hydrolysis of Potato Starch

Studies on Starch Phosphate. Part 2. Isolation of Glucose 3‐Phosphate and Maltose Phosphate by Acid Hydrolysis of Potato Starch

Esters of Glucose-2-Phosphate: Occurrence and Chemistry

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

Contact Info

Product

Resources

About