Natural Products

Overview of natural product topics covered by the Laschat Research Group

Gephyronic Acid

Gephyronic acid is, due to its biological activity and structural similarity with tedanolid and myriaporon, an interesting target compound. It can be retrosynthetically separated into the western and eastern fragment. As these synthetic routes provide both fragments in only moderate yields, therein lies a great potential for a synthetic improvement to the important target compound. It is our goal to realize the synthesis of both fragments in the simplest, cleanest and most cost-effective routes possible, during which derivatives could also be achieved, in order to fully investigate wherein such compounds, the maximum biological activity can be found.

Borrelidine Analogues

The macrolide antibiotic borrelidine is an interesting target compound for several research groups due to its unique structure and its versatile biological activity.[1,2] The natural product was first isolated from Streptomyces rochei in 1949 by Berger et al. as an antibiotic possessing anti-borrelia activity. 
Its biological activity includes, but is not limited to, the selective inhibition of threonyl tRNA synthetase, antiviral as well as antiangiogenesis activities. In order to gain a better understanding of the researching for viable synthetic routes to borrelidine and its analogues and testing them in several cell lines. 

[1] Nagamitsu T., Harigaya Y. Omura S., Proc. Japan Acad Ser. B 2005, 81, 244-256. 
[2] Theurer M., El Bay Y., Koschorreck K., Urlacher Vlada B., Rauhut G., Baro A., and Laschat S. Eur. J. Org. Chem. 2011, 4241-4249. 

Molecular Bionics

Elastin is an important extracellular matrix protein in connective tissue. The unique properties of the skin, such as high elasticity and tensile strength can be attributed to elastin. It is constructed of flexible and water-soluble tropoelastin polymer chains which are connected mainly by the cross-linker desmosine.[1]Inspired by this structure we design new cross-linkers based on pyridinium salts with acrylate or acrylamide as connecting unit.[2] These units can react with thiolated hyaluronic acid by the thio-Michael addition and form a hydrogel.[3]

[1] M. Akagawa, K. Suyama, Connective Tissue Research 2000, 41, 131. 
[2] M. Mateescu et al., Synthesis 2014, 46, 1243-1253. 
[3] V. Hagel et al., Nature Sci. Rep. 2013, 3, 2043 (1-5).

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