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Search for "nucleoside phosphorylases" in Full Text gives 7 result(s) in Beilstein Journal of Organic Chemistry.
Anion exchange resins in phosphate form as versatile carriers for the reactions catalyzed by nucleoside phosphorylases
Beilstein J. Org. Chem. 2020, 16, 2607–2622, doi:10.3762/bjoc.16.212
- ; purine nucleoside phosphorylases; recombinant E. coli uridine; thymidine; Introduction Diverse variants of enzymatic syntheses of nucleosides using nucleoside phosphorylases as biocatalysts have been repeatedly described in original studies and discussed in a number of recent reviews (see, e.g., [1][2
- ][3][4][5][6][7][8][9][10][11][12][13][14][15]). In the late forties and early fifties of the last century, α-ᴅ-pentofuranose-1-phosphates (PF-1Pis) were isolated from the phosphorolysis of natural nucleosides catalyzed by nucleoside phosphorylases and their structures and enzymatic reactions with
- employing nucleoside phosphorylases as biocatalysts. The enzymatic reaction of PF-1Pis and heterocyclic bases is a key step of the transglycosylation strategy for the synthesis of biologically important nucleosides. The reactions of phosphorolysis and interaction of the resulting PF-1Pis with heterocyclic
Recent advances in synthetic approaches for medicinal chemistry of C-nucleosides
Beilstein J. Org. Chem. 2018, 14, 772–785, doi:10.3762/bjoc.14.65
- , synthetic C-nucleosides, such as immucillin-H and GS-5734, have shown potent activity against purine nucleoside phosphorylases (PNP) and broad spectrum antiviral activities. Synthetic approaches to C-nucleosides. A. Two common strategies for C-nucleoside synthesis involve functionalization at C1' and
Acid-catalyzed ring-opening reactions of a cyclopropanated 3-aza-2-oxabicyclo[2.2.1]hept-5-ene with alcohols
Beilstein J. Org. Chem. 2017, 13, 2888–2894, doi:10.3762/bjoc.13.281
- the structure against cleavage by nucleoside phosphorylases or hydrolases [18][19]. The addition of a cyclopropane unit could provide further rigidity that could better stabilize the compound, thereby enhancing its biological activity. Both of these reported ring-openings of cyclopropanated 3-aza-2
Strategies toward protecting group-free glycosylation through selective activation of the anomeric center
Beilstein J. Org. Chem. 2017, 13, 1239–1279, doi:10.3762/bjoc.13.123
- nucleosides [23][24]. The enzymes typically employed for these purposes are nucleoside phosphorylases (NPs) or nucleoside deoxyribosyltransferases (NDTs) in the presence of inorganic phosphate in a tandem enzymatic process [25]. In Scheme 5 we highlight a very recent example of this methodology for the
Enzymatic synthesis and phosphorolysis of 4(2)-thioxo- and 6(5)-azapyrimidine nucleosides by E. coli nucleoside phosphorylases
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
- ; 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
- 2.4.2.4) phosphorylases [36], and (ii) the role of structural features and electronic properties of the pyrimidine bases and nucleosides in the recognition by E. coli nucleoside phosphorylases. Results and Discussion Thioxo- and 6-aza-pyrimidines used in the transglycosylation reaction with recombinant E
The chemoenzymatic synthesis of clofarabine and related 2′-deoxyfluoroarabinosyl nucleosides: the electronic and stereochemical factors determining substrate recognition by E. coli nucleoside phosphorylases
Beilstein J. Org. Chem. 2014, 10, 1657–1669, doi:10.3762/bjoc.10.173
- ab initio calculations in terms of the electronic structure (natural purines vs analogues) and stereochemical features (2FAra-1P vs Ara-1P) of the studied compounds to determine the substrate recognition by E. coli nucleoside phosphorylases. The second approach starts with the cascade one-pot
- 2-chloro-9-(β-D-arabinofuranosyl)adenine (6) in 45 min, the formation of 2-chloro-9-(β-D-xylofuranosyl)adenine (7) proceeded very slowly attaining ca. 8% yield in 48 h. Keywords: chemoenzymatic synthesis; clofarabine; nucleoside phosphorylases; phosphopentomutase; recombinant E. coli ribokinase
- demonstrated that D-ribose and 2-deoxy-D-ribose can be converted to nucleosides in the cascade one-pot synthesis under the consecutive action of three E. coli enzymes, i.e., ribokinase (RK), phosphopentomutase (PPM) and nucleoside phosphorylases [24][25][26][27] (for a recent review, see [28]). In the present
Understanding the mechanism of Pd-catalyzed allylic substitution of the cyclic difluorinated carbonates
Beilstein J. Org. Chem. 2008, 4, No. 18, doi:10.3762/bjoc.4.18
- substitution features a reversal of regioselectivity caused by fluorine. Background Carbocyclic nucleosides (CNAs), in which the furanose oxygen atoms of the 4'-oxonucleosides are substituted by CH2, have received considerable attention because they exhibit greater metabolic stability toward nucleoside
- phosphorylases and higher lipophilicity, two properties that are potentially beneficial in terms of increased in vivo half life, oral efficiency and cell wall penetration [1][2]. Based on CNA skeletons, 1,2-disubstituted carbocyclic nucleosides (OTCs) recently attracted more and more attention [3][4][5][6][7][8
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