31501-46-9Relevant academic research and scientific papers
MODIFIED OLIGOMERIC COMPOUNDS AND USES THEREOF
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, (2021/02/19)
The present disclosure provides oligomeric compounds comprising a modified oligonucleotide having at least one stereo-non-standard nucleoside. An oligomeric compound comprising a modified oligonucleotide consisting of 12-30 linked nucleosides, wherein at least one nucleoside of the modified oligonucleotide is a stereo-non-standard nucleoside; and wherein the oligomeric compound is selected from among an RNAi compound, a modified CRISPR compound, and an artificial mRNA compound.
Total synthesis of 2'-O-methyl-β-L-arabinosyluridine and reassignment the nucleoside from penicillium sp. as 2'-O-methyl-β-L-uridine
Shen, Chunyang,Ding, Haixin,Tao, Xueping,Yang, Ruchun,Bai, Jiang,Cao, Ban-Peng,Peng, Yi-Yuan,Xiao, Qiang
, p. 68 - 72 (2020/01/30)
In order to validate the structure of a rarely reported naturally occurring nucleoside isolated from the broth of Penicillium sp. (NO. 64), practical syntheses of 2′-O-methyl-β-L-arabinosyluridine, 2′-O-methyl-α-L-arabinosyluridine, and 2′-O-methyl-β-L-uridine were accomplished. Comparing their nuclear magnetic resonance (NMR) spectra and physical data, its structure was reassigned as 2′-O-methyl-β-L-uridine instead of former reported 2′-O-methyl-β-L-arabinosyluridine.
Novel nucleoside analogues as effective antiviral agents for Zika virus infections
Bassetto, Marcella,Basso, Mattia,Brancale, Andrea,Bugert, Joachim J.,Cima, Cecilia M.,Friese, Daniela,Salerno, Martina,Schwarze, Frank
, (2020/10/29)
Previously considered a neglected flavivirus, Zika virus has recently emerged as a public health concern due to its ability to spread rapidly and cause severe neurological disorders, such as microcephaly in newborn babies from infected mothers, and Guilla
Novel antiviral activity of l-dideoxy bicyclic nucleoside analogues versus vaccinia and measles viruses in vitro
McGuigan, Christopher,Hinsinger, Karen,Farleigh, Laura,Pathirana, Ranjith N.,Bugert, Joachim J.
, p. 1311 - 1322 (2013/03/29)
Dideoxy bicyclic pyrimidine nucleoside analogues (ddBCNAs) with d-chirality have previously been described by us to inhibit replication of human cytomegalovirus. We herein report for the first time that activity against vaccinia virus (VACV) was achieved
Three-pronged probes: High-affinity DNA binding with cap, β-alanines and oligopyrrolamides
Haug, Ruediger,Kramer, Markus,Richert, Clemens
supporting information, p. 15822 - 15826 (2014/04/03)
TPP oligonucleotides: Hybridization probes that interrogate target sequences through base pairing, stacking on the terminus, and binding in the minor groove are presented (see figure). All subunits of the probes contribute to the target affinity, leading
Facile synthesis and anti-tumor cell activity of Se-containing nucleosides
Lin, Lina,Sheng, Jia,Momin, Razin K.,Du, Quan,Huang, Zhen
experimental part, p. 56 - 66 (2009/04/07)
Many organic compounds containing selenium have shown anticancer effects and some have been used in chemoprevention of cancers and other diseases. Though Se-containing amino acids are generally used for these purposes, the natural nucleosides may also be used as Se-carriers for these important applications. Therefore, we describe here the convenient synthesis of the new 3'-MeSe-thymidine nucleoside and the other uridine and thymidine derivatives modified with MeSe at the 2' and 5' positions, and report their anti-tumor activity against prostate cancer cell lines. Our work demonstrates for the first time anticancer activity of the methylseleno nucleosides. Copyright Taylor & Francis Group, LLC.
Synthesis of beta-L-2'-deoxy nucleosides
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Page/Page column 34-35, (2010/02/11)
An improved process for the preparation of 2′-modified nucleosides and 2′-deoxy-nucleosides, such as, β-L-2′-deoxy-thymidine (LdT), is provided. In particular, the improved process is directed to the synthesis of a 2′-deoxynucleoside that may utilize different starting materials but that proceeds via a chloro-sugar intermediate or via a 2,2′-anhydro-1-furanosyl-nucleobase intermediate. Where an 2,2′-anhydro-1-furanosyl base intermediate is utilized, a reducing agent, such as Red-Al, and a sequestering agent, such as 15-crown-5 ether, that cause an intramolecular displacement reaction and formation of the desired nucleoside product in good yields are employed. An alternative process of the present invention utilizes a 2,2′-anhydro-1-furanosyl base intermediate without a sequestering agent to afford 2′-deoxynucleosides in good yields. The compounds made according to the present invention may be used as intermediates in the preparation of other nucleoside analogues, or may be used directly as antiviral and/or antineoplastic agents.
A new class of Spiegelmers containing 2′-fluoro-nucleotides
Helmling,Moyroud,Schroeder,Roehl,Kleinjung,Stark,Bahrenberg,Gillen,Klussmann,Vonhoff
, p. 1035 - 1038 (2007/10/03)
Synthesis of 2′-fluoro-nucleosides from L-arabinose in order to perform the synthesis of 2′-fluoro-Spiegelmers binding to a neuropeptide.
Enantioselective synthesis and biological evaluation of 5-o-carboranyl pyrimidine nucleosides
Mourier, Nicolas S.,Eleuteri, Alessandra,Hurwitz, Selwyn J.,Tharnish, Phillip M.,Schinazi, Raymond F.
, p. 2759 - 2766 (2007/10/03)
Base-modified carborane-containing nucleosides such as 5-o-carboranyl-2'-deoxyuridine (CDU) when combined with neutrons have potential for the treatment of certain malignancies. Lack of toxicity in various cells, high accumulation in cancer cells and intracellular phosphorylation are desirable characteristics for modified nucleosides used in boron neutron capture therapy (BNCT) for brain tumors and other malignancies. The aim of this work was to synthesize the two β-enantiomers of several 5-o-carboranyl-containing nucleosides. These derivatives may possess favorable properties such as high lipophilicity, high transportability, the ability to be phosphorylated, and resistance to catabolism. β-Isomers of 2',3'-dihydroxynucleosides and analogues containing a heteroatom in the sugar moiety were also synthesized. Carboranyl pyrimidine nucleosides were prepared either from the parent β-D-nucleoside, β-L-nucleoside, or by a coupling reaction. The dioxolane derivative 7Scheme 1Reagents and conditions: (a) 1,1,1,3,3,3-hexamethydisilazane, ammonium sulfate, reflux, 6 h; (b) tin(IV) chloride, CH2Cl2, 0°C, 2h; (c) tetrabutylammonium fluoride, 1 M sol in THF, 0°C, 3h. was prepared by a coupling reaction between protected 5-o-carboranyluracil (8, CU) and the corresponding protected heterocycle. Specific catalysts were used during the N-glycosylation process to favor the formation of the β-isomer. Biological evaluation of these new chiral 5-o-carboranyl pyrimidine derivatives indicated that most of these compounds have low toxicity in a variety of normal and malignant cells and achieved high cellular levels in a lymphoblastoid cell line. Increasing the number of hydroxyl groups on the sugar moiety decreased the cellular accumulation and serum binding to different extents. Five compounds were identified for further biological evaluation as potential agents for BNCT. Copyright (C) 1999 Elsevier Science Ltd.
A stereospecific synthesis of 2',3'-dideoxy-β-L-cytidine (β-L-ddC). A potent inhibitor against human hepatitis B virus (HBV) and human immunodeficiency virus (HIV)
Lin,Luo,Liu
, p. 3477 - 3480 (2007/10/02)
2',3'-Dideoxy-β-L-cytidine (β-L-ddC), a potent inhibitor against human hepatitis B virus (HBV) and human immunodeficiency virus (HIV), has been stereospecifically synthesized from L-arabinose in 9 steps.
