Bioconjugate, nucleoside

Latham-Timmons HA, Wolter A, Roarch JS, Giare R, Leuck M (2003) Novel method for the covalent immobilization of oligonucleotides via Diels-Alder bioconjugation. Nucleosides Nucleotides Nucleic Acids 22 1495-1487... 

Bemdl S, Herzig N, Kele P et al (2009) Comparison of a nucleosidic vs non-nucleosidic postsynthetic click modification of DNA with base-labile fluorescent probes. Bioconjug... 

Figure 27.1 Three common nucleoside triphosphate derivatives that can be incorporated into oligonucleotides by enzymatic means. The first two are biotin derivatives of pyrimidine and purine bases, respectively, that can be added to an existing DNA strand using either polymerase or terminal transferase enzymes. Modification of DNA with these nucleosides results in a probe detectable with labeled avidin or streptavidin conjugates. The third nucleoside triphosphate derivative contains an amine group that can be added to DNA using terminal transferase. The modified oligonucleotide then can be labeled with amine-reactive bioconjugation reagents to create a detectable probe.

Husar GM, Anziano DJ, Leuck M, Sebesta DP (2001) Covalent modification and surface immobilization of nucleic acids via the Diels-Alder bioconjugation method. Nucleosides Nucleotides Nucleic Acids 20 559-566... 

NaraH, Ono A, Matsuda A (1995) Nucleosides and nucleotides. 135. DNA duplex and triplex formation and resistance to nucleolytic degradation of oligodeoxynucleotides containing syn-norspermidine at the 5-position of 2 -deoxyuridine. Bioconjug Chem 6 54—61... 

Haginoya, N. et al. Nucleosides and nucleotides. Synthesis of oHgodeoxyribonucleotides containing 5-(N-aminoalkyl)carbamoyl-2 -deoxyuridines by a new postsynthetic modification method and their thermal stability and nuclease-resistance properties, Bioconjug. Chem., 8,271,1997. 

The high efficiency and simplicity of CuAAC methodology made this reaction suitable for the development of new nucleoside bioconjugates with novel or increased biological properties, altered hydrophobicity, increased bioaffinity, or ability to carry metal ions. 

The CuAAc methodology was used to prepare a variety of nucleoside bioconjugates bearing spin labels or fluorescent probes (compounds 27-30) [40 -43] and was also used for the F-labeling of nucleosides (compound 27G) (Figure 10.5) [44]. 

Figure 10.4 Nucleoside bioconjugates bearing carboranes and c/oso-dodecarborane.

Bioconjugates of nucleosides and Pleuromutilin, a naturally occurring antibacterial agent, have also been prepared and found to display antibacterial activity (compounds 36-41) (Figure 10.9). Interestingly, some of these analogs showed improved affinity to the peptidyl transferase center in the ribosome compared to the natural Pleuromutilin [51]. 

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