129835-18-3Relevant academic research and scientific papers
Mild Periodinane Oxidation of Protected Nucleosides to Give 2'- and 3'-Ketonucleosides. The First Isolation of a Purine 2'-Deoxy-3'-ketonucleoside Derivative
Samano, Vicente,Robins, Morris J.
, p. 5186 - 5188 (1990)
Oxidation of 3',5'- or 2',5'-bis-O-silyl-protected nucleosides with Dess-Martin 12-I-5 periodinane reagent, 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one (I), in dichloromethane gives 2'- or 3'-ketonucleoside derivatives, respectively.Isolation of the first purine 2'-deoxy-3'-ketonucleoside derivative (2d) has been accomplished by periodinane oxidation of 5'-O-(tert-butyldiphenylsilyl)-2'-deoxyadenosine (1d).
NUCLEOTIDE CLEAVABLE LINKERS AND USES THEREOF
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Paragraph 0761, (2020/07/26)
Disclosed herein, inter alia, are compounds, compositions, and methods of use thereof for sequencing a nucleic acid.
NOVEL PHOSPHOROUS (V)-BASED REAGENTS, PROCESSES FOR THE PREPARATION THEREOF, AND THEIR USE IN MAKING STEREO-DEFINED ORGANOPHOSHOROUS (V) COMPOUNDS
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Paragraph 0313-0314, (2019/11/04)
The present invention relates to novel phosphorous (V) (P(V)) reagents, methods for preparing thereof, and methods for preparing organophosphorous (V) compounds by using the novel reagents.
THERMALLY-CLEAVABLE PROTECTING AND LINKER GROUPS
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Page/Page column 8; 49; 50; 86, (2018/11/10)
The present invention relates to chemical linkers and protecting groups, compounds and compositions containing the chemical linkers or protecting groups, and intermediates and processes that can be used to prepare them. The chemical linkers and protecting groups are based on pyrrolidine and piperidine activating groups, which undergo intramolecular cyclisation upon heating with release of carbon dioxide, thereby releasing the organic compound from a substrate. In particular, those chemical linkers and protecting groups are useful in the solid phase synthesis of oligonucleotides according to the following representative schemes.
Synthesis of a deoxyxylopuromycin analogue
Krishnakumar, Kollappillil S.,Strazewski, Peter
experimental part, p. 1055 - 1058 (2010/06/22)
N6-Bis-demethylated deoxyxylopuromycin was synthesized over six steps in 56% overall yield. The key steps are Mitsunobu reaction with DPPA and a Staudinger-Vilarrasa coupling. Georg Thieme Verlag Stuttgart - New York.
Convenient syntheses of 3′-amino-2′,3′- dideoxynucleosides, their 5′-monophosphates, and 3′-aminoterminal oligodeoxynucleotide primers
Eisenhuth, Ralf,Richert, Clemens
body text, p. 26 - 37 (2009/04/07)
(Chemical Equation Presented) 5′-Protected 3′-amino-2′, 3′-dideoxynucleosides containing any of the four canonical nucleobases (A/C/G/T) were prepared via azides in five to six steps, starting from deoxynucleosides. For pyrimidines, the synthetic route in
Design, synthesis and anti flaviviridae activity of N6-, 5′,3′-O- and 5′,2′-O-substituted adenine nucleoside analogs
Angusti, Angela,Manfredini, Stefano,Durini, Elisa,Ciliberti, Nunzia,Vertuani, Silvia,Solaroli, Nicola,Pricl, Sabrina,Ferrone, Marco,Fermeglia, Maurizio,Loddo, Roberta,Secci, Barbara,Visioli, Anna,Sanna, Tiziana,Collu, Gabriella,Pezzullo, Margherita,La Colla, Paolo
experimental part, p. 423 - 432 (2009/04/11)
During a random screening of representative libraries of nucleoside analogues we discovered that the adenine derivatives FEVB28 and FEG118 were Flaviviridae inhibitors endowed with potency comparable, if not superior, to that of ribavirin. Those studies prompted us to design a new class of protected nucleoside analogs, reported herein, which displays interesting anti-bovine viral diarrhea virus (BVDV) activity and low cytotoxicity in cell-based assays (4, 23, 29 EC50: 14, 11, 26 μM respectively, CC50 > 100 μM) and appreciable activity in enzyme assays against the RNA dependent RNA polymerase (RdRp) of BVDV (4, 23, 29, RdRp inhibition activity 27, 16, 15 μM respectively). A molecular modeling study was also carried out to highlight the possible interactions between this compounds class and the corresponding hepatitis C virus (HCV) enzyme.
Effective anomerisation of 2′-deoxyadenosine derivatives during disaccharide nucleoside synthesis
Gulyaeva, Irma V.,Neuvonen, Kari,Loennberg, Harri,Rodionov, Andrei A.,Shcheveleva, Elena V.,Bobkov, Georgii V.,Efimtseva, Ekaterina V.,Mikhailov, Sergey N.
, p. 1849 - 1864 (2007/10/03)
The formation of a disaccharide nucleoside (11) by O3′-glycosylation of 5′-O-protected 2′-deoxyadenosine or its N6-benzoylated derivative has been observed to be accompanied by anomerisation to the corresponding α-anomeric product (12). The latter reaction can be explained by instability of the N-glycosidic bond of purine 2′- deoxynucleosides in the presence of Lewis acids. An independent study on the anomerisation of partly blocked 2′-deoxyadenosine has been carried out. Additionally, transglycosylation has been utilized in the synthesis of 3′-O-β-D-ribofuranosyl-2′-deoxyadenosines and its α-anomer.
Diastereoselective synthesis of α-substituted-γ-butyrolactones of nucleosides via [1,5]-c,h insertion reactions of α-diazomalonates of nucleosides
Lim, Jinsoo,Choo, Dong-Joon,Kim, Yong Hae
, p. 553 - 554 (2007/10/03)
Diastereoselective and regioselective [1,5]-C,H insertion reactions of 2'-deoxy-3'-diazomalonate nucleosides afforded τ-butyrolactones of nucleosides as chiral synthons for the preparation of 2'-C-branched nucleosides.
Anticancer and antiviral effects and inactivation of S-adenosyl-L- homocysteine hydrolase with 5'-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues
Wnuk, Stanislaw F.,Yuan, Chong-Sheng,Borchardt, Ronald T.,Balzarini, Jan,De Clercq, Erik,Robins, Morris J.
, p. 1608 - 1618 (2007/10/03)
Selectively protected adenine nucleosides were converted into 5'- carboxaldehyde analogues by Moffatt oxidation (dimethyl sulfoxide/dicyclohexylcarbodiimide/dichloroacetic acid) or with the Dess- Martin periodinane reagent. Hydrolysis of a 5'-fluoro-5'-S-methyl-5'-thio (α-fluoro thioether) arabinosyl derivative also gave the 5'-carboxaldehyde. Treatment of 5'-carboxaldehydes with hydroxylamine [or O-(methyl, ethyl, and benzyl)hydroxylamine] hydrochloride gave E/Z oximes. Treatment of purified oximes with aqueous trifluoroacetic acid and acetone effected trans-oximation to provide clean samples of 5'-carboxaldehydes. Adenosine (Ado)-5'- carboxaldehyde and its 4'-epimer are potent inhibitors of S-adenosyl-L- homocysteine (AdoHcy) hydrolase. They bind efficiently to the enzyme and undergo oxidation at C3' to give 3'-keto analogues with concomitant reduction of the NAD+ cofactor to give an inactive, tightly bound NADH-enzyme complex (type I cofactor-depletion inhibition). Potent type I inhibition was observed with 5'-carboxaldehydes that contain a ribo cis-2',3'-glycol. Their oxime derivatives are 'proinhibitors' that undergo enzyme-catalyzed hydrolysis to release the inhibitors at the active site. The 2'-deoxy and 2'-epimeric (arabinosyl) analogues were much weaker inhibitors, and the 3'-deoxy compounds bind very weakly. Ado-5'-carboxaldehyde oxime had potent cytotoxicity in tumor cell lines and was toxic to normal human cells. Analogues had weaker cytotoxic and antiviral potencies, and the 3'-deoxy compounds were essentially devoid of cytotoxic and antiviral activity.
