Beta-Amino acids containing natural products and analogs: Efrapeptins

The natural product efrapeptin C was first synthesised by a new synthetic strategy. Besides β-alanine, efrapeptin C contains seven α-aminoisobutyric acid residues which enormously hampers the synthesis by conventional methods. A new modular solid phase synthesis concept suitable for using α-azido-isobutyric acid chloride as equivalent for activated aminoisobutyric acid facilitates parallel synthesis of efrapeptin C and its analogues. Structural investigations using NMR spectroscopy (including residual dipolar couplings) and molecular dynamics calculations as well as CD spectroscopy and bioassays (ATPase-Inhibition) are currently being performed.

The First Total Synthesis of Efrapeptin C
M. Jost, J.-C. Greie, N. Stemmer, S. D. Wilking, K. Altendorf, N. Sewald
Angew. Chem., 114 (2002) 4438-4440; Angew. Chem. Int. Ed. Engl., 41 (2002) 4267-4269.

People involved:
Dr. Thomas Huber, Dr. Micha Jost, Dr. Sven Weigelt, Dr. Sven D. Wilking

Prof. Dr. Karlheinz Altendorf, Osnabrück; Dr. Zsuzsa Majer, Budapest; Prof. Dr. Andrea Melandri, Bologna; Prof. Dr. Horst Kessler, München; Dr. Burkhard Luy, München


Here you find Information about the projects of the workgroup Organic Chemistry III.