16205-60-0Relevant articles and documents
Nucleobase-Functionalized 5-Aza-7-deazaguanine Ribo- A nd 2′-Deoxyribonucleosides: Glycosylation, Pd-Assisted Cross-Coupling, and Photophysical Properties
Leonard, Peter,Kondhare, Dasharath,Jentgens, Xenia,Daniliuc, Constantin,Seela, Frank
supporting information, p. 13313 - 13328 (2019/11/11)
The special nucleobase recognition pattern of 5-aza-7-deazaguanine nucleosides makes them valuable for construction of homo purine DNA, silver-mediated base pairs, and expansion of the four letter genetic coding system. To widen the utility of 5-aza-7-deazaguanine nucleosides, side chains were introduced at position-7 of the nucleobase. As key compounds, 7-iodo nucleosides were synthesized. Nucleobase anion glycosylation of the iodo derivative of isobutyrylated 5-aza-7-deazaguanine with the bromo sugar of 2,3,5-tri-O-benzoyl-1-O-acetyl-d-ribofuranose gave the pure β-D anomeric N-9 glycosylation product (67%), whereas one-pot Vorbrüggen conditions gave only 42% of the iodinated nucleoside. The noniodinated nucleoside was formed in 84%. For the synthesis of 2′-deoxyribonucleosides, anion glycosylation performed with Hoffer's 2′-deoxyhalogenose yielded an anomeric mixture (α-D = 33% and β-D = 39%) of 2′-deoxyribonucleosides. Various side chain derivatives were prepared from nonprotected nucleosides by Pd-assisted Sonogashira or Suzuki-Miyaura cross-coupling. Among the functionalized ribonucleosides and anomeric 2′-deoxyribonucleosides, some of them showed strong fluorescence. Benzofuran and pyrene derivatives display high quantum yields in non-aqueous solvents and solvatochromism. Single-crystal X-ray analysis of 7-iodo-5-aza-7-deaza-2′-deoxyguanosine displayed intermolecular iodo-oxygen interactions in the crystal and channels filled with solvent molecules.
Engineering the substrate specificity of ADP-ribosyltransferases for identifying direct protein targets
Carter-O'Connell, Ian,Jin, Haihong,Morgan, Rory K.,David, Larry L.,Cohen, Michael S.
supporting information, p. 5201 - 5204 (2014/05/06)
Adenosine diphosphate ribosyltransferases (ARTDs; ARTD1-17 in humans) are emerging as critical regulators of cell function in both normal physiology and disease. These enzymes transfer the ADP-ribose moiety from its substrate, nicotinamide adenine dinucle
Synthesis of ribonucleosides of 2-thioxopyrido [2,3-d]pyrimidines by phase transfer catalysis and their antimicrobial activity
Agrawal, Hemlata,Swati,Yadav, Ashok K.,Prakash, Lalit
, p. 159 - 166 (2007/10/03)
The ribonucleosides viz; 2-thioxo-3,5,7-trisubstituted-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl) pyrido[2,3-d]pyrimidine-4 (1H)-ones have been synthesized via phase transfer ribosylation of 2-thioxo- 3,5,7-trisubstituted pyrido[2,3-d)pyrimidine-4(1H)-ones with 2,3,5-tri-O-benzoyl-β-D- ribofuranosyl bromide in biphasic solvent such as CH2Cl2-50% aqueous NaOH using tetrabutylammonium bromide as phase transfer catalysis (PTC). The synthesized compounds have been characterized by elemental analyses, spectral data and screened for their antimicrobial activity.