- A Scalable Synthesis of α-L-Threose Nucleic Acid Monomers
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Recent advances in polymerase engineering have made it possible to copy information back and forth between DNA and artificial genetic polymers composed of TNA (α-l-threofuranosyl-(3′,2′) nucleic acid). This property, coupled with enhanced nuclease stability relative to natural DNA and RNA, warrants further investigation into the structural and functional properties of TNA as an artificial genetic polymer for synthetic biology. Here, we report a highly optimized chemical synthesis protocol for constructing multigram quantities of TNA nucleosides that can be readily converted to nucleoside 2′-phosphoramidites or 3′-triphosphates for solid-phase and polymerase-mediated synthesis, respectively. The synthetic protocol involves 10 chemical transformations with three crystallization steps and a single chromatographic purification, which results in an overall yield of 16-23% depending on the identity of the nucleoside (A, C, G, T).
- Sau, Sujay P.,Fahmi, Nour Eddine,Liao, Jen-Yu.,Bala, Saikat,Chaput, John C.
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- Efficient construction of a stable linear gene based on a TNA loop modified primer pair for gene delivery
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A terminal-closed linear gene with strong exonuclease resistance and serum stability was successfully constructed by polymerase chain reaction (PCR) with an α-l-threose nucleic acid (TNA) loop modified primer pair, which can be used as an efficient gene e
- Ding, Baoquan,Han, Lin,Liu, Jianbing,Lu, Xuehe,Wu, Tiantian,Wu, Xiaohui
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supporting information
p. 9894 - 9897
(2020/09/09)
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- NOVEL ANTIVIRAL COMPOUNDS, A PROCESS FOR THEIR PREPARATION, AND THEIR USE FOR TREATING VIRAL INFECTIONS
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The present invention relates to novel pro-drugs of L-2'-deoxythreose nucleoside phosphonates, such as phosphoramidate, phosphorodiamidate and phospho-diester prodrugs. The invention also relates to a process for preparing these novel prodrugs of nucleoside phosphonates. The invention also relates to the use of these novel phosphonatemodified nucleosides to treat or prevent viral infections and their use to manufacture a medicine to treat or prevent viral infections, particularly infections with viruses belonging to the HBV family.
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Page/Page column 21; 22
(2017/01/05)
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- Synthesis and polymerase incorporation of β,γ-modified α-L-threofuranosyl thymine triphosphate mimics
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Three β,γ-modified α-L-threofuranosyl nucleoside triphosphates were synthesized. The β,γ-modified tTTPs undergo a single incorporation event with HIV RT but undergo multiple incorporations to form full-length product with engineered thermophilic polymeras
- Chen, Zhe,Meek, Kirsten N.,Rangel, Alexandra E.,Heemstra, Jennifer M.
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p. 3958 - 3962
(2016/08/01)
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- Synthesis of α- L -threose nucleoside phosphonates via regioselective sugar protection
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A new synthesis route to α-l-threose nucleoside phosphonates via 2-O and 3-O selectively protected l-threose is developed. The key intermediates 2-O-benzoyl-l-threonolactone and 1-O-acetyl-2-O-benzoyl-3-O-t- butyldiphenylsilyl-l-threofuranose were functionalized to synthesize 2′-deoxy-2′-fluoro- and 3′-C-ethynyl l-threose 3′-O-phosphonate nucleosides. The key intermediates developed are important intermediates for the synthesis of new l-threose-based nucleoside analogues, TNA phosphoramidites, and TNA triphosphates.
- Dumbre, Shrinivas G.,Jang, Mi-Yeon,Herdewijn, Piet
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p. 7137 - 7144
(2013/08/23)
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