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Amino Linker Oligonucleotide Modification

Primary alkyamino modified oligonucleotides are commonly used in oligonucleotide labeling and conjugations towards such electrophilic moieties as active esters, halogenated aliphatic and aromatic derivatives1.  

In general, labeling oligonucleotides with different reporter molecules requires a post-synthetic solution phase process, where both amino labeled oligonucleotide and the corresponding reporter NHS ester are dissolved in an aqueous organic solvent system. It is important that both reacting synthons are completely soluble in the reaction mixture.  Another important requirement for the reaction to be successful is that the reaction mixture is basic enough to drive the coupling reaction to completion and that the active ester is stable at least for the duration of the reaction.

3’-Amino modified oligonucleotides demonstrated resistance to 3’-exonuclease activity2 and are also used as efficient polymerase chain terminator or a 3’-blocking group.

Bio-synthesis offers not only a wide variety of 3’-, 5’- and internally amino modified oligonucleotides but also their conjugates with peptides, proteins and antibodies1.

5' Amino Modifications

  • 5' C3 Amino Linker
  • 5' C6 Amino Linker
  • 5' C12 Amino Linker
  • 5' Amino Modifier 5
  • 5' Amino TEG (triethylene glycol 12 atoms)
  • 5' PC Amino Linker

3' Amino Modifications

  • 3' C3 Amino Linker
  • 3' C6 Amino Linker
  • 3' Amino C6 dC
  • 3' Amino C6 dT
  • 3' C7 Amino Linker

Internal Amino Modifications

  • 2'-Deoxyadenosine-8-C6 Amino Linker (Amino C6 dA)
  • 2'-Deoxycytidine-5-C6 Amino Linker (Amino C6 dC)
  • 2'-Deoxyguanosine-8-C6 Amino Linker (Amino C6 dG)
  • C7 Internal Amino Linker
  • Thymidine-5-C2 Amino Linker (Amino C2 dT)
  • Thymidine-5-C6 Amino Linker (Amino C6 dT)

 

 Reference:

  1. http://www.biosyn.com/Bioconjugation.aspx

  2. Zendegui, J. G.; Vasquez, K. M.; Tinsley, J. H.; Kessler, D. J.; Hogan, M. E., Nucleic Acids Res., 1992, 20, 307.