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Anion exchange resins in phosphate form as versatile carriers for the reactions catalyzed by nucleoside phosphorylases.


ABSTRACT: In the present work, we suggested anion exchange resins in the phosphate form as a source of phosphate, one of the substrates of the phosphorolysis of uridine, thymidine, and 1-(?-?-arabinofuranosyl)uracil (Ara-U) catalyzed by recombinant E. coli uridine (UP) and thymidine (TP) phosphorylases. ?-?-Pentofuranose-1-phosphates (PF-1Pis) obtained by phosphorolysis were used in the enzymatic synthesis of nucleosides. It was found that phosphorolysis of uridine, thymidine, and Ara-U in the presence of Dowex® 1X8 (phosphate; Dowex-nPi) proceeded smoothly in the presence of magnesium cations in water at 20-50 °C for 54-96 h giving rise to quantitative formation of the corresponding pyrimidine bases and PF-1Pis. The resulting PF-1Pis can be used in three routes: (1) preparation of barium salts of PF-1Pis, (2) synthesis of nucleosides by reacting the crude PF-1Pi with an heterocyclic base, and (3) synthesis of nucleosides by reacting the ionically bound PF-1Pi to the resin with an heterocyclic base. These three approaches were tested in the synthesis of nelarabine, kinetin riboside, and cladribine with good to excellent yields (52-93%).

SUBMITTER: Artsemyeva JN 

PROVIDER: S-EPMC7588730 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Anion exchange resins in phosphate form as versatile carriers for the reactions catalyzed by nucleoside phosphorylases.

Artsemyeva Julia N JN   Remeeva Ekaterina A EA   Buravskaya Tatiana N TN   Konstantinova Irina D ID   Esipov Roman S RS   Miroshnikov Anatoly I AI   Litvinko Natalia M NM   Mikhailopulo Igor A IA  

Beilstein journal of organic chemistry 20201022


In the present work, we suggested anion exchange resins in the phosphate form as a source of phosphate, one of the substrates of the phosphorolysis of uridine, thymidine, and 1-(β-ᴅ-arabinofuranosyl)uracil (Ara-U) catalyzed by recombinant <i>E. coli</i> uridine (UP) and thymidine (TP) phosphorylases. α-ᴅ-Pentofuranose-1-phosphates (PF-1Pis) obtained by phosphorolysis were used in the enzymatic synthesis of nucleosides. It was found that phosphorolysis of uridine, thymidine, and Ara-U in the pres  ...[more]

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