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Org Lett. 2014 May 2;16(9):2414-7. doi: 10.1021/ol500779s. Epub 2014 Apr 15.

Cystomanamides: structure and biosynthetic pathway of a family of glycosylated lipopeptides from myxobacteria.

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Department of Microbial Natural Products, Helmholtz-Institute for Pharmaceutical Research Saarland (HIPS), Helmholtz Centre for Infection Research (HZI) and Pharmaceutical Biotechnology, Saarland University , Campus C2 3, 66123 Saarbrücken, Germany.


Cystomanamides A-D were isolated as novel natural product scaffolds from Cystobacter fuscus MCy9118, and their structures were established by spectroscopic techniques including 2D NMR, LC-SPE-NMR/-MS, and HR-MS. The cystomanamides contain β-hydroxy amino acids along with 3-amino-9-methyldecanoic acid that is N-glycosylated in cystomanamide C and D. The gene cluster for cystomanamide biosynthesis was identified by gene disruption as PKS/NRPS hybrid incorporating an iso-fatty acid as starter unit and including a reductive amination step at the interface of the PKS and NRPS modules.

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