Make or break: the thermodynamic equilibrium of polyphosphate kinase-catalysed reactions

• Michael Keppler,
• Sandra Moser,
• Henning J. Jessen,
• Christoph Held and
• Jennifer N. Andexer

Beilstein J. Org. Chem. 2022, 18, 1278–1288, doi:10.3762/bjoc.18.134

• reaction with AMP (via ADP) to ATP (2.5% AMP/27.5% ADP/70% ATP) [16]. In theory, the addition of another, ideally irreversible reaction can be used to pull the equilibrium further to the product side. Another recent application of PPKs in the cascade synthesis of cladribine triphosphate (2-chloro-2

• equilibrium. In fact, the authors observed an (compared to the adenosine-to-ATP cascades) increased yield of 80% cladribine triphosphate, with 2-Cl-dADP being the major byproduct [22]. The incomplete conversion (despite the irreversible reduction step) has been explained by the previously mentioned myokinase

• . Nevertheless, as it becomes evident from the cladribine system, exactly this broad substrate range might be disadvantageous, thus highlighting the necessity to tailor the choice of enzymes to the substrates and reaction sequence in question. In ATP regeneration systems, the equilibrium issue might be less

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

• in cladribine synthesis The dual function of QAE Sephadex A-25 noted above was tested in the enzymatic synthesis of cladribine using dRib-1Pi as a barium salt and bound to the resin. Chemical synthesis of this nucleoside, which has a wide spectrum of pharmacological activities [6][63][64][65], is

• wearisome [5][66]. This evidence prompted us to engage in the design and development of an efficient biotechnological synthetic route. Cladribine has been known for over 30 years as antineoplastic (Leustatine®) and anti-multiple sclerosis agent (for a few leading references, see [67][68][69][70]). The

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

• reactions on the 6-chloropurine nucleosides. Intermediate compounds 31–40 were deprotected with a saturated solution of ammonia in methanol to furnish the desired products 6–15 in 70–92% yields (Table 1). 3’-Fluoro-2-chloropurine nucleosides – cladribine and clofarabine mimics Anticancer drugs cladribine

N-Alkyl derivatives of diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside; synthesis and antimicrobial activity

• Agata Walczewska,
• Daria Grzywacz,
• Dorota Bednarczyk,
• Małgorzata Dawgul,
• Andrzej Nowacki,
• Wojciech Kamysz,
• Beata Liberek and
• Henryk Myszka

Beilstein J. Org. Chem. 2015, 11, 869–874, doi:10.3762/bjoc.11.97

• demonstrated that diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside hydrochloride increases the number of apoptotic B cells, in combination with cladribine (2-CdA), which were isolated from chronic lymphotic leukemia (B-CLL) patients [40]. The presence of the amine group in this promising antitumor compound