Flexible Alkyne-Linked Thymidine Phosphoramidites and Triphosphates for Chemical or Polymerase Synthesis and Fast Postsynthetic DNA Functionalization through Copper-Catalyzed Alkyne Azide 1,3-Dipolar Cycloaddition

0492075 - ÚOCHB 2019 RIV US eng J - Journal Article
Panattoni, Alessandro - Pohl, Radek - Hocek, Michal
Flexible Alkyne-Linked Thymidine Phosphoramidites and Triphosphates for Chemical or Polymerase Synthesis and Fast Postsynthetic DNA Functionalization through Copper-Catalyzed Alkyne Azide 1,3-Dipolar Cycloaddition.
Organic Letters. Roč. 20, č. 13 (2018), s. 3962-3965. ISSN 1523-7060. E-ISSN 1523-7052
R&D Projects: GA MŠMT(CZ) EF16_019/0000729; GA ČR(CZ) GA18-03305S
EU Projects: European Commission(XE) 642023 - ClickGene
Grant - others:AV ČR(CZ) AP1501
Program: Akademická prémie - Praemium Academiae
Institutional support: RVO:61388963
Keywords : click reaction * nucleic acids * oligonucleotides
OECD category: Organic chemistry
Impact factor: 6.555, year: 2018
https://pubs.acs.org/doi/10.1021/acs.orglett.8b01533

Two alternative flexible alkyne-linked thymine nucleosides (propargyl-diethylene glycol- or undecyn-linked 5-hydroxymethyluracil derivatives), as well as their phosphoramidites and triphosphates, were designed and synthesized. The nucleoside 3'-O-phosphoramidites were successfully incorporated into oligonucleotides on a solid support, whereas the nucleoside triphosphates served as good substrates for polymerase synthesis of modified DNA, which underwent fast and efficient copper-catalyzed alkyne azide 1,3-dipolar cycloaddition (CuAAC) reactions.
Permanent Link: http://hdl.handle.net/11104/0285955