Mg(II) ion-mediated conversion of mono- and oligonucleotides to 5′-polyphosphates in aqueous solution

Sawai, Hiroaki; Inaba, Yoshiko; Hirano, Atsushi; Wakai, Hiromichi; Shimazu, Masamitsu

doi:10.1016/s0040-4039(00)74092-5

Cited by 3 publications

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“…Curiously, in some cases small amounts of triphosphates were produced during the synthesis of the diphosphates. Similar side reactions have previously been observed . Nucleoside monophosphates ( 11a − g , Scheme ) were obtained by hydrolyzing the nucleoside 5‘-dichlorophosphates 7a − g by treatment with triethylammonium hydrogen bicarbonate buffer.…”

Section: Synthesissupporting

confidence: 55%

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Synthesis and Structure−Activity Relationships of Uracil Nucleotide Derivatives and Analogues as Agonists at Human P2Y₂, P2Y₄, and P2Y₆ Receptors

2006

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A series of UTP, UDP, and UMP derivatives and analogues were synthesized and evaluated at the human pyrimidinergic P2Y receptor subtypes P2Y2, P2Y4, and P2Y6 stably expressed in 1321N1 astrocytoma cells. Substituents at N3 of UTP were poorly tolerated by P2Y2 and P2Y4 receptors. In contrast, a large phenacyl substituent at N3 of UDP was well tolerated by the P2Y6 receptor, yielding a potent and selective P2Y6 receptor agonist (3-phenacyl-UDP, EC50=70 nM, >500-fold selective). The most potent and selective P2Y2 receptor agonist of the present series was 2-thio-UTP (EC50=50 nM, >or=30-fold selective vs P2Y4 and P2Y6). All modifications at the uracil base of UTP led to a decrease in potency at the P2Y4 receptor. A beta,gamma-dichloromethylene modification in the triphosphate chain of 5-bromo-UTP was tolerated by all three receptor subtypes, thus opening up a new strategy to obtain ectonucleotide diphosphohydrolase- and phosphatase-resistant P2Y2, P2Y4, and P2Y6 receptor agonists.

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Section: Synthesissupporting

confidence: 55%

“…Similar side reactions have previously been observed. 30 Nucleoside monophosphates (11a-g, Scheme 1) were obtained by hydrolyzing the nucleoside 5′-dichlorophosphates 7a-g by treatment with triethylammonium hydrogen bicarbonate buffer.…”

Section: Synthesismentioning

confidence: 99%

Synthesis and Structure−Activity Relationships of Uracil Nucleotide Derivatives and Analogues as Agonists at Human P2Y₂, P2Y₄, and P2Y₆ Receptors

2006

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Mononucleotides

Frank¹

2013

Chemistry of Plant Phosphorus Compounds

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2013

Chemistry of Plant Phosphorus Compounds

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Mg(II) ion-mediated conversion of mono- and oligonucleotides to 5′-polyphosphates in aqueous solution

Cited by 3 publications

References 12 publications

Synthesis and Structure−Activity Relationships of Uracil Nucleotide Derivatives and Analogues as Agonists at Human P2Y₂, P2Y₄, and P2Y₆ Receptors

Synthesis and Structure−Activity Relationships of Uracil Nucleotide Derivatives and Analogues as Agonists at Human P2Y₂, P2Y₄, and P2Y₆ Receptors

Mononucleotides

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Mg(II) ion-mediated conversion of mono- and oligonucleotides to 5′-polyphosphates in aqueous solution

Cited by 3 publications

References 12 publications

Synthesis and Structure−Activity Relationships of Uracil Nucleotide Derivatives and Analogues as Agonists at Human P2Y2, P2Y4, and P2Y6 Receptors

Synthesis and Structure−Activity Relationships of Uracil Nucleotide Derivatives and Analogues as Agonists at Human P2Y2, P2Y4, and P2Y6 Receptors

Mononucleotides

References

Contact Info

Product

Resources

About

Synthesis and Structure−Activity Relationships of Uracil Nucleotide Derivatives and Analogues as Agonists at Human P2Y₂, P2Y₄, and P2Y₆ Receptors

Synthesis and Structure−Activity Relationships of Uracil Nucleotide Derivatives and Analogues as Agonists at Human P2Y₂, P2Y₄, and P2Y₆ Receptors