Phosphorylation of Martotriose With Inorganic Cyclo-Triphosphate

Inoue, Hideko; Tone, Naoto; Tsuhako, Mitsutomo; Eguchi, Taro

doi:10.3363/prb1992.16.0_11

Cited by 10 publications

(7 citation statements)

References 8 publications

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“…Previously, we reported that alkylamines 8 , amino acid 9 , aminoalcohols 10 , and carbohydrates [11][12][13][14][15][16] readily phosphorylated with P 3m to give their triphosphate derivatives. Organic compounds containing amino or hydroxyl group were easily phosphorylated by P 3m .…”

Section: Structure Of Theanine (Thea)mentioning

confidence: 99%

Phosphorylation of Theanine With Cyclo-Triphosphate in Aqueous Solution

Maeda

Kanazawa

Komatsu

et al. 2015

Phosphorus Research Bulletin

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Phosphorylation of theanine (Thea) has been achieved using inorganic cyclo-triphosphate (P 3m ) in aqueous solution. The optimum condition for the phosphorylation of Thea with P 3m is Thea : P 3m = 2.0 M : 0.5 M, pH 11 and 10 ºC. N 2 -(Phosphono)theanine was synthesized with the yield of more than 90 % and then remained constant after 40 d without hydrolysis of the monophosphate derivative. The phosphorylated product of Thea has a N-P bond in the molecule. The reaction mechanism of Thea with P 3m was discussed.

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Section: Structure Of Theanine (Thea)mentioning

confidence: 99%

Phosphorylation of Theanine With Cyclo-Triphosphate in Aqueous Solution

Maeda

Kanazawa

Komatsu

et al. 2015

Phosphorus Research Bulletin

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“…The main phosphorylated products were 2Ј-and 3Ј-monophosphate esters of the nucleosides and nucleotides. We also reported that alkylamines, 11) aminoalcohols, 12) and carbohydrates [13][14][15][16][17][18] are readily phosphorylated with P 3m to give the corresponding triphosphate derivatives. Unfortunately, phosphorylated carbohydrates are easily decomposed to monophosphate derivatives.…”

mentioning

confidence: 99%

“…Unfortunately, phosphorylated carbohydrates are easily decomposed to monophosphate derivatives. 9,10,[13][14][15][16][17][18] We have developed new inorganic phosphorylating reagents, imido-cyclo-triphosphates, Na 3 P 3 O 9Ϫn (NH) n . Compared with the P-O-P linkage, the P-NH-P linkage is stable and difficult to hydrolyze.…”

mentioning

confidence: 99%

Phosphorylation of Nucleosides and Nucleotides with Inorganic Monoimido-cyclo-Triphosphate

Maeda

Chiba

Tsuhako

2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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Nucleosides and related organic compounds are usually phosphorylated by phosphoryl chloride, 1) polyphosphoric acid [2][3][4] and various organic phosphorus compounds. [5][6][7][8] Because phosphorylation with these agents is accompanied by various side reactions, protection of other functional groups is necessary and complicated procedures are typically required.Sodium cyclo-triphosphate, Na 3 P 3 O 9 (P 3m ), is a simple and efficient inorganic phosphorylating agent. One of the authors reported the phosphorylation of nucleosides 9) and nucleotides 10) by P 3m . The 2Ј-and 3Ј-OH groups of the b-D-ribofuranosyl unit on nucleosides and nucleotides were selectively phosphorylated in high yield without the need for protection of the other hydroxyl groups. The main phosphorylated products were 2Ј-and 3Ј-monophosphate esters of the nucleosides and nucleotides. We also reported that alkylamines, 11) aminoalcohols, 12) and carbohydrates [13][14][15][16][17][18] are readily phosphorylated with P 3m to give the corresponding triphosphate derivatives. Unfortunately, phosphorylated carbohydrates are easily decomposed to monophosphate derivatives. 9,10,[13][14][15][16][17][18] We have developed new inorganic phosphorylating reagents, imido-cyclo-triphosphates, Na 3 P 3 O 9Ϫn (NH) n . Compared with the P-O-P linkage, the P-NH-P linkage is stable and difficult to hydrolyze. 19) We therefore explored the use of imido-cyclo-triphosphates for the phosphorylation of biologically important compounds. Monoimido-cyclo-triphosphate (MCTP), diimido-cyclo-triphosphate (DCTP), and triimidocyclo-triphosphate (TCTP), shown in Fig. 1, were synthesized. Our current interest is to disclose the phosphorylation mechanism by MCTP and DCTP. TCTP did not react even under strict conditions such as pH 13 and 70°C.MCTP is a six-membered ring composed of one P-NH-P and two P-O-P linkages. We recently demonstrated that the phosphorylation of methylamine 20) and amino acids 21) proceeded with MCTP. More recently, we reported that D-glucose, D-glucuronic acid and 2-deoxy-D-glucose reacted with MCTP to form 1-O-diphosphoramidophosphono-b-D-aldoses stereoselectively.22) Organic compounds containing amino or hydroxyl group were easily phosphorylated by MCTP. We also reported that D-glucose and gluco-oligosaccharides reacted with DCTP. 23)In the present work, we chose MCTP and first studied the reaction of nucleosides with MCTP in aqueous solution, followed by phosphorylation of nucleotides, in order to synthesize triphosphate derivatives of nucleosides and nucleotides. Results and DiscussionPhosphorylation of Adenosine (1), Guanosine (2), Cytidine (3) and Uridine (4) with MCTP Nucleosides used in the present study are shown in Fig. 2. Phosphorylation was carried out essentially according to the previously described The phosphorylation of nucleosides (adenosine, guanosine, cytidine, and uridine) and nucleotides (adenosine 5-monophosphate, guanosine 5-monophosphate, cytidine 5-monophosphate and uridine 5-monophosphate) has been achieved using inorganic monoi...

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“…[3][4][5] This reaction was found to be applicable to other monosaccharides and oligosaccharides. [6][7][8] Unfortunately, the products formed from carbohydrates are easily decomposed to monophosphate derivatives.Imido-cyclo-triphosphates, Na 3 P 3 O 9Ϫn (NH) n , have been known since 1962. 9) Compared with the P-O-P linkage, the P-NH-P linkage is stable and difficult to hydrolyze.…”

mentioning

confidence: 99%

“…Previously, we reported that alkylamines, 1) aminoalcohols, 2) and carbohydrates [3][4][5][6][7][8] are readily phosphorylated with P 3m to give their triphosphate derivatives. In particular, the reaction of D-glucose with P 3m in aqueous solution afforded 1-O-triphospho-b-D-glucose stereoselectively in good yield (47%) in a one-step process without protection of hydroxyl groups.…”

mentioning

confidence: 99%

Phosphorylation of D-Glucose Derivatives with Inorganic Monoimido-cyclo-triphosphate

Inoue

Yamada

Tsuhako

2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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Sodium cyclo-triphosphate, Na 3 P 3 O 9 (P 3m ), is a simple and efficient phosphorylating agent. Previously, we reported that alkylamines, 1) aminoalcohols, 2) and carbohydrates [3][4][5][6][7][8] are readily phosphorylated with P 3m to give their triphosphate derivatives. In particular, the reaction of D-glucose with P 3m in aqueous solution afforded 1-O-triphospho-b-D-glucose stereoselectively in good yield (47%) in a one-step process without protection of hydroxyl groups. [3][4][5] This reaction was found to be applicable to other monosaccharides and oligosaccharides. [6][7][8] Unfortunately, the products formed from carbohydrates are easily decomposed to monophosphate derivatives.Imido-cyclo-triphosphates, Na 3 P 3 O 9Ϫn (NH) n , have been known since 1962. 9) Compared with the P-O-P linkage, the P-NH-P linkage is stable and difficult to hydrolyze. 9) We therefore explored the use of monoimido-cyclo-triphosphate (MCTP) for the phosphorylation of biologically important compounds. The structure of MCTP is shown in Chart 1: the six-membered ring is composed of one P-NH-P and two P-O-P linkages. We recently demonstrated that the phosphorylation of methylamine 10) and amino acids 11) proceeded with MCTP. More recently, we reported that cyclodextrins reacted with MCTP to form 2-O-diphosphoramidophosphonocyclodextrins regioselectively in aqueous solution.12) Organic compounds containing an amino or a hydroxyl group were easily phosphorylated by MCTP. Kamasaka et al. 13) have reported that phosphoryl oligosaccharides had the ability to form a soluble complex with calcium and had an inhibitory effect on the formation of calciumphosphate precipitate. Moreover, phosphoryl oligosaccharides effectively enhanced remineralization of enamel and dentin lesion. From the point of chelating of calcium by them, triphosphoryl saccharides lead to an advantageous food ingredient as a soluble calcium. This ability would be improved by diphosphoramidophosphate ester because it was not hydrolyzed to the imidophosphate ester and diphosphate.In the present work, we first studied the reaction of D-glucose with MCTP in aqueous solution, and then investigated the phosphorylation of D-glucose derivatives by MCTP in order to develop a one-step synthesis of phosphorylated monosaccharides. Results and DiscussionPhosphorylation of D-Glucose (1), D-Glucuronic Acid (2) and 2-Deoxy-D-glucose (3) with MCTP D-Glucose (1) and its derivatives used in the present study are shown in Table 1. Phosphorylation was carried out essentially according to the previously described method.10-12) Figure 1 shows HPLC profiles for the reaction mixture of D-glucose (1) (1.5 M) and MCTP (0.3 M) incubated at pH 12 and 25°C. A peak attributed to the phosphorylated product (4) appeared at a retention time of about 20 min. The other chromatographic peaks were assigned to MCTP and its hydrolytic product (monoimidotriphosphate, MTP), respectively.To identify the product 4,

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Phosphorylation of Martotriose With Inorganic Cyclo-Triphosphate

Cited by 10 publications

References 8 publications

Phosphorylation of Theanine With Cyclo-Triphosphate in Aqueous Solution

Phosphorylation of Theanine With Cyclo-Triphosphate in Aqueous Solution

Phosphorylation of Nucleosides and Nucleotides with Inorganic Monoimido-cyclo-Triphosphate

Phosphorylation of D-Glucose Derivatives with Inorganic Monoimido-cyclo-triphosphate

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