Chloromyxamide

Chloromyxamides were identificied as a family of chlorinated peptides from the myxobacterium Myxococcussp. MCy10608 based on high-resolution mass spectrometric data. NMR spectroscopy in combination with mass spectrometric analysis showed that these peptides contain the unprecedented chlori­nated amino acid 6-chloromethyl-5-methoxypipecolic acid.

  • M. Meusel, F. Hufsky, F. Panter, D. Krug, R. Müller, S. Böcker, Anal. Chem. 2016, 88, 7556.
 

Full structural elucidation, total synthesis and biosynthesis of chloromyxamides was performed. Chemical synthesis – including a remarkable approach to access the CMPA unit – was pursued to confirm the structure of chloromyxamides and enabled determination of the absolute stereochemistry in the CMPA ring.

  • J. Gorges, L. Kjaerulff, F. Panter, T. Hoffmann, U. Kazmaier, R. Müller, "Structure, total synthesis and biosynthesis of Chloromyxamides - myxobacterial tetrapeptides featuring an uncommon 6-chloromethyl-5-methoxypipecolic acid building block", Angew. Chem. 2018, 130, 14466–14471; Angew. Chem.Int.Ed. 2018, 57, 14270–14275.