Beilstein J. Org. Chem.2017,13, 1430–1438, doi:10.3762/bjoc.13.140
BASF SE, 67056 Ludwigshafen, Germany 10.3762/bjoc.13.140 Abstract Two hitherto unknown fusaricidins were obtained from fermentation broths of three Paenibacillus strains. After structure elucidation based on tandem mass spectrometry and NMR spectroscopy, fusaricidin E was synthesized to confirm the
structure and the suggested stereochemistry. The synthesis was based on a new strategy which includes an efficient access to the 15-guanidino-3-hydroxypentadecanoyl (GHPD) side chain from erucamide.
Keywords: cyclodepsipeptides; fusaricidins; lipopeptides; structure elucidation; total synthesis
; Introduction
Fusaricidins are lipid-modified non-ribosomal cyclic hexadepsipeptides containing four D-amino acids and two L-amino acids. All of them carry an L-threonine linked to a unique 15-guanidino-3-hydroxypentadecanoic acid side chain through the N-terminus. This particular ω-functionalized lipid side
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Graphical Abstract
Figure 1:
Structure of fusaricidins E (1) and F (2).
Beilstein J. Org. Chem.2012,8, 1344–1351, doi:10.3762/bjoc.8.154
difficult to determine structure–activity relationships [7][8]. More recently, the solid-phase synthesis of a number of analogues of the fusaricidins has been reported. However, in all cases, the side chain 3-hydroxy group was not incorporated into the structure [9]. By total synthesis of both side-chain