Thermophilic phosphoribosyltransferases Thermus thermophilus HB27 in nucleotide synthesis

• Ilja V. Fateev,
• Ekaterina V. Sinitsina,
• Aiguzel U. Bikanasova,
• Maria A. Kostromina,
• Elena S. Tuzova,
• Larisa V. Esipova,
• Tatiana I. Muravyova,
• Alexei L. Kayushin,
• Irina D. Konstantinova and
• Roman S. Esipov

Beilstein J. Org. Chem. 2018, 14, 3098–3105, doi:10.3762/bjoc.14.289

• atoms. Probably, the presence of nitrogen atom at C7 position of purine heterocycles plays an important role in reactions catalyzed by phosphoribosyltransferase, and also affects the substrate properties of TthHPRT and TthAPRT. Two nucleotides were synthesized using TthHPRT or TthAPRT (see Figure 6

Investigation of the action of poly(ADP-ribose)-synthesising enzymes on NAD⁺ analogues

• Sarah Wallrodt,
• Edward L. Simpson and
• Andreas Marx

Beilstein J. Org. Chem. 2017, 13, 495–501, doi:10.3762/bjoc.13.49

• -step procedure (Supporting Information File 1, Scheme S1). Next, NAD+ substrate properties were investigated in ADP-ribosylation assays with histone H1.2 as acceptor and in ARTD automodification. For a better comparison, the assay conditions for ARTD2, ARTD5 and ARTD6 were chosen to be similar and were

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

• % and 15% yields, respectively. 6-Azauracil and 6-azathymine showed good substrate properties for both TP and UP, whereas only TP recognizes 2-thio-6-azathymine as a substrate. 5-Phenyl and 5-tert-butyl derivatives of 6-azauracil and its 2-thioxo derivative were tested as substrates for UP and TP, and

• ; recombinant E. coli uridine, thymidine and purine nucleoside phosphorylases; substrate properties; 4(2)-thioxo- and 6(5)-aza-uacil and -thymine; Introduction Nucleosides of 4- and 2-thioxopyrimidines and 6-azapyrimidines attract much attention from the time of pioneering works in the early 1950s on the

• . coli nucleoside phosphorylases and 2'-deoxyguanosine as a donor of 2-deoxy-D-ribofuranose: The substrate properties of 4-thiouracil (1a; 4SUra), 2-thiouracil (2a; 2SUra), 6-azauracil (3a), 6-azathymine (4a) and 6-aza-2-thiothymine (5a) for the recombinant E. coli TP and UP in the transglycosylation

The chemoenzymatic synthesis of clofarabine and related 2′-deoxyfluoroarabinosyl nucleosides: the electronic and stereochemical factors determining substrate recognition by E. coli nucleoside phosphorylases

• Ilja V. Fateev,
• Konstantin V. Antonov,
• Irina D. Konstantinova,
• Tatyana I. Muravyova,
• Frank Seela,
• Roman S. Esipov,
• Anatoly I. Miroshnikov and
• Igor A. Mikhailopulo

Beilstein J. Org. Chem. 2014, 10, 1657–1669, doi:10.3762/bjoc.10.173

• study, we described the synthesis of the phosphate 12a by the modified MacDonald method and investigated its substrate properties for the recombinant E. coli nucleoside phosphorylases. In particular, we focused on reactions with a number of purine bases (2-chloroadenine, 2-aminoadenine and hypoxanthine

• a productive transition state of the base and 12a. The good substrate properties of the phosphate 12a prompted us to test it in the enzymatic synthesis of base-modified nucleosides 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-aza-7-deazaguanine (4a; purine numbering) and 9-(2-deoxy-2-fluoro-β-D

• -pentose. D-Arabinose and its derivatives D-arabinofuranose-5-phosphate and α-D-arabinofuranose-1-phosphate showed good substrate properties for the corresponding E. coli RK, PPM and PNP, and the desired 9-(β-D-arabinofuranosyl)-2-chloroadenine (6) was formed in ca. 54% yield in 45 min, after which the 2