Anion exchange resins in phosphate form as versatile carriers for the reactions catalyzed by nucleoside phosphorylases
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 E. coli uridine (UP) and thymidine (TP) phosphorylases. α-ᴅ-P...
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2020-10-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.16.212 |
| _version_ | 1819291595742117888 |
|---|---|
| author | Julia N. Artsemyeva Ekaterina A. Remeeva Tatiana N. Buravskaya Irina D. Konstantinova Roman S. Esipov Anatoly I. Miroshnikov Natalia M. Litvinko Igor A. Mikhailopulo |
| author_facet | Julia N. Artsemyeva Ekaterina A. Remeeva Tatiana N. Buravskaya Irina D. Konstantinova Roman S. Esipov Anatoly I. Miroshnikov Natalia M. Litvinko Igor A. Mikhailopulo |
| author_sort | Julia N. Artsemyeva |
| collection | DOAJ |
| description | 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 E. coli 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 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%). |
| first_indexed | 2024-12-24T03:41:08Z |
| format | Article |
| id | doaj.art-629ea6a1bcea484e97d3d9df7ed67155 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-24T03:41:08Z |
| publishDate | 2020-10-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-629ea6a1bcea484e97d3d9df7ed671552022-12-21T17:16:53ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972020-10-011612607262210.3762/bjoc.16.2121860-5397-16-212Anion exchange resins in phosphate form as versatile carriers for the reactions catalyzed by nucleoside phosphorylasesJulia N. Artsemyeva0Ekaterina A. Remeeva1Tatiana N. Buravskaya2Irina D. Konstantinova3Roman S. Esipov4Anatoly I. Miroshnikov5Natalia M. Litvinko6Igor A. Mikhailopulo7Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, 220141 Minsk, Acad. Kuprevicha 5/2, Republic of BelarusInstitute of Bioorganic Chemistry, National Academy of Sciences of Belarus, 220141 Minsk, Acad. Kuprevicha 5/2, Republic of BelarusInstitute of Bioorganic Chemistry, National Academy of Sciences of Belarus, 220141 Minsk, Acad. Kuprevicha 5/2, Republic of BelarusShemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya 16/10, 117997 GSP-7, Moscow B-437, Russian FederationShemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya 16/10, 117997 GSP-7, Moscow B-437, Russian FederationShemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya 16/10, 117997 GSP-7, Moscow B-437, Russian FederationInstitute of Bioorganic Chemistry, National Academy of Sciences of Belarus, 220141 Minsk, Acad. Kuprevicha 5/2, Republic of BelarusInstitute of Bioorganic Chemistry, National Academy of Sciences of Belarus, 220141 Minsk, Acad. Kuprevicha 5/2, Republic of BelarusIn 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 E. coli 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 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%).https://doi.org/10.3762/bjoc.16.212anion exchange resinsn6-benzyladenosinecladribineenzymatic glycosylationkinetin ribosidenelarabineα-ᴅ-pentofuranose-1-phosphatesphosphorolysis of nucleosidespurine nucleoside phosphorylasesrecombinant e. coli uridinethymidine |
| spellingShingle | Julia N. Artsemyeva Ekaterina A. Remeeva Tatiana N. Buravskaya Irina D. Konstantinova Roman S. Esipov Anatoly I. Miroshnikov Natalia M. Litvinko Igor A. Mikhailopulo Anion exchange resins in phosphate form as versatile carriers for the reactions catalyzed by nucleoside phosphorylases Beilstein Journal of Organic Chemistry anion exchange resins n6-benzyladenosine cladribine enzymatic glycosylation kinetin riboside nelarabine α-ᴅ-pentofuranose-1-phosphates phosphorolysis of nucleosides purine nucleoside phosphorylases recombinant e. coli uridine thymidine |
| title | Anion exchange resins in phosphate form as versatile carriers for the reactions catalyzed by nucleoside phosphorylases |
| title_full | Anion exchange resins in phosphate form as versatile carriers for the reactions catalyzed by nucleoside phosphorylases |
| title_fullStr | Anion exchange resins in phosphate form as versatile carriers for the reactions catalyzed by nucleoside phosphorylases |
| title_full_unstemmed | Anion exchange resins in phosphate form as versatile carriers for the reactions catalyzed by nucleoside phosphorylases |
| title_short | Anion exchange resins in phosphate form as versatile carriers for the reactions catalyzed by nucleoside phosphorylases |
| title_sort | anion exchange resins in phosphate form as versatile carriers for the reactions catalyzed by nucleoside phosphorylases |
| topic | anion exchange resins n6-benzyladenosine cladribine enzymatic glycosylation kinetin riboside nelarabine α-ᴅ-pentofuranose-1-phosphates phosphorolysis of nucleosides purine nucleoside phosphorylases recombinant e. coli uridine thymidine |
| url | https://doi.org/10.3762/bjoc.16.212 |
| work_keys_str_mv | AT julianartsemyeva anionexchangeresinsinphosphateformasversatilecarriersforthereactionscatalyzedbynucleosidephosphorylases AT ekaterinaaremeeva anionexchangeresinsinphosphateformasversatilecarriersforthereactionscatalyzedbynucleosidephosphorylases AT tatiananburavskaya anionexchangeresinsinphosphateformasversatilecarriersforthereactionscatalyzedbynucleosidephosphorylases AT irinadkonstantinova anionexchangeresinsinphosphateformasversatilecarriersforthereactionscatalyzedbynucleosidephosphorylases AT romansesipov anionexchangeresinsinphosphateformasversatilecarriersforthereactionscatalyzedbynucleosidephosphorylases AT anatolyimiroshnikov anionexchangeresinsinphosphateformasversatilecarriersforthereactionscatalyzedbynucleosidephosphorylases AT nataliamlitvinko anionexchangeresinsinphosphateformasversatilecarriersforthereactionscatalyzedbynucleosidephosphorylases AT igoramikhailopulo anionexchangeresinsinphosphateformasversatilecarriersforthereactionscatalyzedbynucleosidephosphorylases |