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

• products (≥98%) were obtained: Fludarabine 94% after 3 h, yield 77%; hypoxanthine-arabinoside 90% after 168 h, yield 81%, and nelarabine 50% after 36 h, yield 40%, respectively [42]. Earlier, Krenitsky et al. described the synthesis of nelarabine [43] and fludarabine [44] using the transglycosylation

• the transarabinosylation of 2-fluoroadenine (UP 8.7 IU and PNP 93.3 IU; 4 mM K-phosphate buffer, pH 7.0; 864 h at 35 °C; 14%) [44] vs the condensation of Ara-1Pi and 2-fluoroadenine (water, 360 IU of PNP; 3 h at 55 °C; 77%) [42], and a comparable efficiency of nelarabine synthesis, viz., PNP 37,800 IU

Versatile synthesis and biological evaluation of novel 3’-fluorinated purine nucleosides

• Hang Ren,
• Haoyun An,
• Paul J. Hatala,
• William C. Stevens Jr,
• Jingchao Tao and
• Baicheng He

Beilstein J. Org. Chem. 2015, 11, 2509–2520, doi:10.3762/bjoc.11.272

• , nelarabine, cladribine, and clofarabine are an important subset of nucleoside drugs [7][8][9][10]. Purine ribonucleosides substituted at position 6 have exhibited potent antimetabolite activity [11][12][13] and aryl or heterocyclic substituents have imparted cytostatic activities against various tumor cell