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

• Julia N. Artsemyeva,
• Ekaterina A. Remeeva,
• Tatiana N. Buravskaya,
• Irina D. Konstantinova,
• Roman S. Esipov,
• Anatoly I. Miroshnikov,
• Natalia M. Litvinko and
• Igor A. Mikhailopulo

Beilstein J. Org. Chem. 2020, 16, 2607–2622, doi:10.3762/bjoc.16.212

• were tested in the synthesis of nelarabine, kinetin riboside, and cladribine with good to excellent yields (52–93%). Keywords: anion exchange resins; N6-benzyladenosine; cladribine; enzymatic glycosylation; kinetin riboside; nelarabine; α-ᴅ-pentofuranose-1-phosphates; phosphorolysis of nucleosides

• formation of N6-benzylaminopurine riboside (BAPR; N6-benzyladenosine) was monitored by HPLC. A reference BAPR sample was obtained in 67% yield by the transglycosylation of BAP using a combination of guanosine and E. coli PNP to generate in situ Rib-1Pi (for the synthesis and NMR data, see Supporting

• ) as biocatalysts at 23 °C for 50 h. Synthesis of nelarabine with intermediate preparation of crude Ara-1Pi. Synthesis of kinetin riboside with intermediate preparation of crude Rib-1Pi. Synthesis of N6-benzyladenosine (BAPR) employing Rib-1Pi ionically bound with indicated resins (phosphate form