Isolation of a new disaccharide nucleoside from Helleborus caucasicus: structure elucidation and total synthesis of hellecaucaside A and its β-anomer

Sylla, Balla; Gauthier, Charles; Legault, Jean; Fleury, Pierre-Yves; Lavoie, Serge; Mshvildadze, Vakhtang; Muzashvili, T; Kemertelidze, Eter; Pichette, André

doi:10.1016/j.carres.2014.06.027

Cited by 15 publications

(8 citation statements)

References 27 publications

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“…[49] The described glycosylation of 3 ,5 -O-TIPDS-protected uridine with 1-thiotolyl-2,3,5-tri-O-benzyl-Dribofuranoside under AgOTf/N -iodosuccinimide catalysis proceeded with high yield (82%) of blocked 2 -O-α-D-ribofuranosyluridine. SCHEME 5 Pyrophosphate modification of oligodeoxynucleotides.…”

Section: Synthesis Of Disaccharide Nucleosidesmentioning

confidence: 98%

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

Drenichev

Mikhailov

2015

Nucleosides, Nucleotides and Nucleic Acids

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Poly(ADP-ribose) (PAR) is a natural polymer, taking part in numerous important cellular processes. Several enzymes are involved in biosynthesis and degradation of PAR. One of them, poly(ADP-ribose)polymerase-1 (PARP-1) is considered to be a perspective target for the design of new drugs, affecting PAR metabolism. The structure of PAR was established by enzymatic hydrolysis and further analysis of the products, but total chemical synthesis of PAR hasn't been described yet. Several approaches have been developed on the way to chemical synthesis of this unique biopolymer.

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Section: Synthesis Of Disaccharide Nucleosidesmentioning

confidence: 98%

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

Drenichev

Mikhailov

2015

Nucleosides, Nucleotides and Nucleic Acids

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“…Disaccharide nucleosides constitute a widespread and important group of natural compounds, 38,39,68 which have been isolated from Streptomyces sp., 69 yeast RNA hydrolyzates 68 and marine organisms. 70,71 Disaccharide nucleosides exist not only in free state, but also as the components of bioacitve molecules such as tRNA 72 , antibiotics and PAR. 68 The common structural feature of disaccharide nucleosides is that they all have extra pyranose or furanose moiety connected to nucleoside at 2'-, 3'-or 5'-OH.…”

Section: Chemical Synthesis Of Poly(adp-ribose)mentioning

confidence: 99%

Poly(ADP-ribose): the structure and the synthesis

Zhao¹,

Wu²,

Li³

2020

Arkivoc

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Poly(ADP-ribose) belongs to a momentous post-translational modification of eukaryotic nuclear protein.Protein poly(ADP-ribosyl)ation mediates numerous cell signalings and is related to some diseases. Poly(ADPribose) is currently available through enzymatic or chemical synthesis. Herein, we summarize the structure characteristics and recent developments in the synthesis of poly(ADP-ribose) from a chemical point of view.

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“…Using method 2 (Table 1), Hellecaucaside A, a new natural nucleoside, isolated from the roots of Helleborus caucasicus, was obtained for the first time. 39 Recently diglycosylated adenosine 15, which represents the branching motif of PAR, was prepared. 42 The two obvious steps for its synthesis are glycosylation of selectively protected 2 0 -O-a-D-ribofuranosyladenosine or introduction of adenine moiety into corresponding trisaccharide.…”

Section: Introductionmentioning

confidence: 99%