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

Intramolecular glycosylation

• Xiao G. Jia and
• Alexei V. Demchenko

Beilstein J. Org. Chem. 2017, 13, 2028–2048, doi:10.3762/bjoc.13.201

• very first experiments performed by Arthur Michael and Emil Fischer in the late 1800’s, the glycosylation reaction remains challenging to chemists. Enzymatic glycosylation reactions are highly stereoselective [33]. However, the stereocontrol of chemical glycosylation reactions remains cumbersome

Strategies toward protecting group-free glycosylation through selective activation of the anomeric center

• A. Michael Downey and
• Michal Hocek

Beilstein J. Org. Chem. 2017, 13, 1239–1279, doi:10.3762/bjoc.13.123

• ligation of an oxazoline donor and commercially available RNase B protein (with the glycans curtailed to a single GlcNAc moiety [17]) as the acceptor [16]. The beauty of this work extends beyond the enzymatic glycosylation reaction. We point out that the oxazoline functionality was installed chemically in

• -enzymatic glycosylation procedure. After extensive optimization, the authors obtained the regioselective C3′-glycosylated sucrose analog in very good yield with complete inversion of stereochemistry at the anomeric position (Scheme 16) by using Ca(OTf)2 and NMe3 (aq). Two of the most remarkable substrates

Enzymatic synthesis and phosphorolysis of 4(2)-thioxo- and 6(5)-azapyrimidine nucleosides by E. coli nucleoside phosphorylases

• Vladimir A. Stepchenko,
• Anatoly I. Miroshnikov,
• Frank Seela and
• Igor A. Mikhailopulo

Beilstein J. Org. Chem. 2016, 12, 2588–2601, doi:10.3762/bjoc.12.254

• only 5-phenyl- and 5-tert-butyl-6-azauracils displayed very low substrate activity. The role of structural peculiarities and electronic properties in the substrate recognition by E. coli nucleoside phosphorylases is discussed. Keywords: enzymatic glycosylation; PM3 and ab initio calculations

• extract of Streptococcus faecalis as biocatalysts [26]. Later on, the conversion of 6-azapyrimidines into their ribonucleosides was observed during the cultivation of Streptococcus faecalis [27][28] and E. coli [29] cells, as well as an enzymatic glycosylation of 14C-labeled 6-azapyrimidines employing the

A selective and mild glycosylation method of natural phenolic alcohols

• Mária Mastihubová and
• Monika Poláková

Beilstein J. Org. Chem. 2016, 12, 524–530, doi:10.3762/bjoc.12.51

• organic media or ionic liquids as co-solvents [24][25][26][27]. The enzymatic transglucosylation using 4-nitrophenyl β-D-glucopyranoside as the donor and almond β-glucosidase as biocatalyst gave salidroside (2) in moderate yield [28]. Recently, we have published the enzymatic glycosylation of tyrosol (2