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Versatile synthesis of amino acid functionalized nucleosides via a domino carboxamidation reaction

Vicky Gheerardijn (UGent) , Jos Van den Begin (UGent) and Annemieke Madder (UGent)
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Abstract
Functionalized oligonucleotides have recently gained increased attention for incorporation in modified nucleic acid structures both for the design of aptamers with enhanced binding properties as well as the construction of catalytic DNA and RNA. As a shortcut alternative to the incorporation of multiple modified residues, each bearing one extra functional group, we present here a straightforward method for direct linking of functionalized amino acids to the nucleoside base, thus equipping the nucleoside with two extra functionalities at once. As a proof of principle, we have introduced three amino acids with functional groups frequently used as key-intermediates in DNA- and RNAzymes via an efficient and straightforward domino carboxamidation reaction.
Keywords
bioorganic chemistry, carboxamidation reaction, amino acids, PROTECTING GROUPS, TRIETHYLAMINE TRIHYDROFLUORIDE, TRANSFER HYDROGENATION, RNA, OLIGONUCLEOTIDES, PEPTIDES, CLEAVAGE, chemically modified, DNA nucleosides, nucleic acids, IN-VITRO SELECTION, DNA DELIVERY-SYSTEMS, NUCLEIC-ACIDS

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Citation

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Chicago
Gheerardijn, Vicky, Jos Van den Begin, and Annemieke Madder. 2014. “Versatile Synthesis of Amino Acid Functionalized Nucleosides via a Domino Carboxamidation Reaction.” Beilstein Journal of Organic Chemistry 10: 2566–2572.
APA
Gheerardijn, V., Van den Begin, J., & Madder, A. (2014). Versatile synthesis of amino acid functionalized nucleosides via a domino carboxamidation reaction. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 10, 2566–2572.
Vancouver
1.
Gheerardijn V, Van den Begin J, Madder A. Versatile synthesis of amino acid functionalized nucleosides via a domino carboxamidation reaction. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. 2014;10:2566–72.
MLA
Gheerardijn, Vicky, Jos Van den Begin, and Annemieke Madder. “Versatile Synthesis of Amino Acid Functionalized Nucleosides via a Domino Carboxamidation Reaction.” BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 10 (2014): 2566–2572. Print.
@article{5902680,
  abstract     = {Functionalized oligonucleotides have recently gained increased attention for incorporation in modified nucleic acid structures both for the design of aptamers with enhanced binding properties as well as the construction of catalytic DNA and RNA. As a shortcut alternative to the incorporation of multiple modified residues, each bearing one extra functional group, we present here a straightforward method for direct linking of functionalized amino acids to the nucleoside base, thus equipping the nucleoside with two extra functionalities at once. As a proof of principle, we have introduced three amino acids with functional groups frequently used as key-intermediates in DNA- and RNAzymes via an efficient and straightforward domino carboxamidation reaction.},
  author       = {Gheerardijn, Vicky and Van den Begin, Jos and Madder, Annemieke},
  issn         = {1860-5397},
  journal      = {BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY},
  language     = {eng},
  pages        = {2566--2572},
  title        = {Versatile synthesis of amino acid functionalized nucleosides via a domino carboxamidation reaction},
  url          = {http://dx.doi.org/10.3762/bjoc.10.268},
  volume       = {10},
  year         = {2014},
}

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