Synthesis and Properties of O‐β‐D‐ribofuranosyl‐(1″→2′)‐guanosine‐5″‐ O‐phosphate and Its Derivatives

Abstract

The efficient synthesis of O‐β‐D‐ribofuranosyl‐(1″→2′)‐guanosine‐5″‐O‐phosphate and O‐β‐D‐ribofuranosyl‐(1″→2′)‐adenosine‐5″‐O‐phosphate, minor tRNA components, have been developed, and their conformational properties were examined by NMR spectroscopy.

LC-MS based quantification of 2′-ribosylated nucleosides Ar(p) and Gr(p) in tRNA

“…13 However, in our hands this reaction gave consistently poor yields. Instead, the simpler 1-Ac-2,3,5-Bz-protected d 2 -ribose 16 was used (Scheme 3).…”

Poly(ADP-ribose): From chemical synthesis to drug design

“…The closest natural analogs of disaccharide monomeric unit of PAR are minor tRNA components-2 0 -O-b-D-ribofuranosyladenosine 5 00 -phosphate, Arp (5) and its guanosine derivative-Grp (6). [11][12][13] The structure of PAR has some similarity to the structure of nucleic acids, since antibodies against PAR can recognize RNA and DNA. 1 Therefore, proteins participating in key cellular processes, such as DNA synthesis and repair, transcription, modulation of chromatin structure can directly or indirectly interact with PAR.…”

“…Base modified NAD-analogs, such as 1,N 6 -etheno-NAD + (e-NAD + ), NGD + , NHD + (Fig. 2) and also 13 C, 15 N-NAD + (not shown), are utilized by PARP-1 and allow the preparation of fluorescent 28 or isotopically labeled PAR. 29 Introduction of propargyl group into adenine moiety of NAD + (Fig.…”

Poly(ADP-Ribose)—A Unique Natural Polymer Structural Features, Biological Role and Approaches to the Chemical Synthesis

“…[3,10] 2 -O-β-D-ribofuranosyladenosine Arp (5) and its guanosine derivative-Grp (6) were isolated from tRNA. [12][13][14] The greatest difference in 1 H-NMR spectrum of monomeric unit 1 in comparison to 2 -O-(5 -O-phospho-β-D-ribofuranosyl-1-yl)-adenosine 5, the closest natural analogue of 1, is observed in coupling constants of the extra carbohydrate moiety due to the difference in configurations of C-1 atoms. Configuration of O-glycosidic bond in isolated nucleosides was unambiguously established by comparative analysis of 13 C-NMR spectra of 2 and anomeric methyl-D-ribofuranosides.…”