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 | Zendy

Alessandro Panattoni | Zendy; Radek Pohl | Zendy; Michal Hocek | Zendy

Open Access

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

Author(s) -

Alessandro Panattoni,

Radek Pohl,

Michal Hocek

Publication year - 2018

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.8b01533

Subject(s) - alkyne , chemistry , cycloaddition , thymine , nucleoside , azide , combinatorial chemistry , oligonucleotide , catalysis , dna polymerase , thymidine , dna , organic chemistry , stereochemistry , biochemistry

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.

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