Organic Chemistry, Department of Chemistry

Organic Chemistry

General
Staff
Current research

General

The main part of the research in organic chemistry deals with synthesis and isolation/characterization of organic compounds. Synthetic work will often be based on the assumption that a given compound or class of compounds possesses certain properties, whether physical, chemical or biological. The research in organic chemistry at Department of Chemistry is aimed at

1) Synthesis of nucleosides and DNA analogues, including development of drugs

The nucleic acid chemistry research area is now included in the Nucleic Acid Center

2) Synthesis of supramolecular compounds, including development of nanoscale electronic systems
3) Studies of reactive intermediates or unstable organic compounds by Flash Vacuum Pyrolysis (FVP) technique.

For a complete structure determination of chemical compounds an X-ray crystallographic examination may sometimes be demanded. At Department of Chemistry X-ray crystallographic methods are used, both within organic and inorganic research.

1) Synthesis of Nucleosides and DNA Analogues, Including Development of Drugs

The starting point for using nucleosides and DNA analogues as drugs was the discovery that certain nucleosides show antiviral activity. Medical treatment with nucleosides, however, is often accompanied by a number of adverse side effects, and in the treatment of e.g. AIDS, the nucleosides are unable to cure the disease, although they help to improve the lives of the patients. As for DNA analogues, the idea of their biological activities is based on the knowledge of the genetic regulation of cell activities. If the order of nucleosides in a given gene is known, and thereby also in the corresponding mRNA, an appropriately designed DNA analogue will be able to bind itself selectively to the mRNA strand. Thus, the synthesis of a certain protein will be inhibited, and the information flow in the cells will stop. The conditions for successful application of this strategy are numerous. For instance, it is necessary that the DNA analogues can penetrate into the cells, and that they are stable towards degradative nucleases.

In the case of both the nucleosides and the DNA analogues it is necessary to synthesize many compounds to hope for the discovery of a potential drug, and on the way it is necessary to develop and improve the synthetic procedures.

2) Supramolecular Chemistry

Molecular biological systems, e.g. the photosynthetic system, are characterized by the fact that they consist of molecular units that are organized in well-ordered structures of nanometer size. During the last few years many research groups have demonstrated that it is possible to synthesize relatively simple complementary molecular building blocks that - via molecular recognition - build up complicated structures, so to speak by themselves. These discoveries are of far-reaching importance. Synthesis of molecular systems and polymers may result in entirely new materials and systems that e.g. will be able to store information on a molecular level (molecular electronics) or act as molecular machines. The research at Department of Chemistry within this field is particularly focused on synthesis of macrocyclic compounds containing electron donors and -acceptors in complementary compounds. These must be able to organize themselves both in solution and in solid phase by means of molecular recognition. The formed complexes could be shaped like e.g. belts, knots, cryptands and catenanes. At the fundamental level this research also includes heterocyclic chemistry, especially sulfur-based heterocycles.

3) Studies of Reactive Intermediates or Unstable Organic Compounds by Flash Vacuum Pyrolysis (FVP) Technique

Reactive intermediates or unstable organic compounds are studied by Flash Vacuum Pyrolysis (FVP) technique where organic compounds are vaporized in high vacuum and pyrolysed in an oven at 500-100°C. The compounds or fragments formed in the pyrolysis are immediately cooled down to 10K and isolated in a matrix of solid Argon, where they can be further studied. The method can also be used preparatively for synthesis or larger amounts of compounds. It is for example possible to study heterocumulenes with a large number of cumulated double bonds. These compounds are of great interest as they have been observed by astrophysicists in the interstellar space. Such compounds are too unstable to be synthesized by normal laboratory methods. In particular, the formation of such compounds from the pyrolysis of 1,2-dithiole derivatives is studied in a more general study of the chemistry of 1,2-dithiole derived compounds.

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