1977•Agricultural and Biological ChemistryOpen access

A new phosphorylating agent, 2-methythio-4H-1,3,2-benzodioxaphosphorin-2-oxide. III. Chemical conversion of ribonucleoside 5'-methylphosphorothiolates into ribonucleotide anhydrides including adenosine 5'-triphosphate and uridine diphosphate glucose.

Masayoshi Iio, Ken-ichi YANO, Masayoshi Eto, Hirohisa Omura, Morifusa Etō

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Abstract

Ribonucleotide anhydrides have been prepared from corresponding ribonucleoside 5'-S-methyl phosphorothiolates by demethylthiolation with iodine in dry pyridine at room temperature in the presence of appropriate phosphates such as inorganic orthophosphate, inorganic pyrophosphate or glucose 1-phosphate. Thus synthesis of ribonucleotide anhydrides have been achieved and three ribonucleoside 5'-triphosphates (ATP, CTP and UTP), three ribonucleoside 5'-diphosphates (ADP, CDP and UDP) and a pyrophosphate coenzyme (UDPG) have been synthesized and isolated as lithium salts by charcoal treatment followed by ion exchange chromatography.

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Ribonucleotide anhydrides have been prepared from corresponding ribonucleoside 5'-S-methyl phosphorothiolates by demethylthiolation with iodine in dry pyridine at room temperature in the presence of appropriate phosphates such as inorganic orthophosphate, inorganic pyrophosphate or glucose 1-phosphate. Thus synthesis of ribonucleotide anhydrides have been achieved and three ribonucleoside 5'-triphosphates (ATP, CTP and UTP), three ribonucleoside 5'-diphosphates (ADP, CDP and UDP) and a pyrophosphate coenzyme (UDPG) have been synthesized and isolated as lithium salts by charcoal treatment followed by ion exchange chromatography.

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Available abstract

Ribonucleotide anhydrides have been prepared from corresponding ribonucleoside 5'-S-methyl phosphorothiolates by demethylthiolation with iodine in dry pyridine at room temperature in the presence of appropriate phosphates such as inorganic orthophosphate, inorganic pyrophosphate or glucose 1-phosphate. Thus synthesis of ribonucleotide anhydrides have been achieved and three ribonucleoside 5'-triphosphates (ATP, CTP and UTP), three ribonucleoside 5'-diphosphates (ADP, CDP and UDP) and a pyrophosphate coenzyme (UDPG) have been synthesized and isolated as lithium salts by charcoal treatment followed by ion exchange chromatography.

Key concepts: Ribonucleoside, Ribonucleotide, Chemistry, Pyrophosphate, Uridine, Nucleotide, Biochemistry, RNA

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A new phosphorylating agent, 2-methythio-4H-1,3,2-benzodioxaphosphorin-2-oxide. III. Chemical conversion of ribonucleoside 5'-methylphosphorothiolates into ribonucleotide anhydrides including adenosine 5'-triphosphate and uridine diphosphate glucose. — Research Paper | ScholarLens