Organic Synthesis

With a background in organic synthesis Kurt Gothelf’s research is founded upon organic chemistry and around half of the members in the groups engage in organic synthesis, often in relation to DNA conjugation.

Among our current synthesis activities are:

  • Synthesis of nucleoside analogues
  • Synthesis of monomers for conjugated polymers and graphene nanoribbons
  • Synthesis of compounds for supramolecular surface chemistry
  • Synthesis of phorphoramidites of linkers and ligands for DNA synthesis
  • Automated DNA synthesis
  • Development of new methods in DNA conjugation, such as light activatable acyl groups

Some of our past contributions to this field are:

Nucleoside analogues

Figure 1

  • Highly stable triple helix formation by homopyrimidine (L)-acyclic threoninol nucleic acids with single stranded DNA and RNA. Vipin Kumar, Venkitasamy Kesavan and Kurt V. Gothelf in press
  • Synthesis, Dynamic Combinatorial Chemistry, and PCR Amplification of 3’–5’ and 3’–6’ Disulfide-linked Oligonucleotides. Hansen, D. J.; Manuguerra, I.; Kjelstrup, M. B.; Gothelf, K. V. Chem. 2014, Early view, DOI: 10.1002/anie.201405761 

Molecules for Supramolecular surface chemistry

  • Synthesis of homochiral tris-indanyl molecular rods. Kjeldsen, N.; Funder, E. D.; Gothelf, K. V. Biomol. Chem. 2014, 12, 3679-3685.
  • Controlling chiral organization of molecular rods on Au(111) by molecular design. Knudsen, M. K.; Kalashnyk, N.; Masini, F.; Cramer, J. R.; Lægsgaard, E.; Besenbacher, F.; Linderoth, T. R.; Gothelf., K. V. Am. Chem. Soc. 2011, 133, 4896–4905.
  • For further examples see under Surface self-assembly

Figure 2

Linkers for bioorganic chemistry

  • Figure 3A cleavable amino-thiol linker for reversible linking of amines to DNA. Højfeldt, J. W.; Blakskjær, P.; Gothelf, K. V. J. Org. Chem. 2006, 71, 9556–9557.

N-Arylation of DNA basesFigure 4

  • Efficient N-arylation and N-alkenylation of the five DNA/RNA nucleobases. Jacobsen, M. F., Knudsen, M. M.; Gothelf, K. V. Org. Chem. 2006, 71, 9183–9190.
  • Efficient N-arylation and N-alkenylation of the five DNA/RNA nucleobases. Jacobsen, M. F., Knudsen, M. M.; Gothelf, K. V. Org. Chem. 2006, 71, 9183–9190.
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