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. 2017 Apr 7;19(7):1772-1775.
doi: 10.1021/acs.orglett.7b00545. Epub 2017 Mar 22.

Linear Peptides Are the Major Products of a Biosynthetic Pathway That Encodes for Cyclic Depsipeptides

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Linear Peptides Are the Major Products of a Biosynthetic Pathway That Encodes for Cyclic Depsipeptides

Thomas P Wyche et al. Org Lett. .

Abstract

Three new dentigerumycin analogues are produced by Streptomyces sp. M41, a bacterium isolated from a South African termite, Macrotermes natalensis. The structures of the complex nonribosomal peptide synthetase-polyketide synthase (NRPS/PKS) hybrid compounds were determined by 1D- and 2D-NMR spectroscopy, high-resolution mass spectrometry, and circular dichroism (CD) spectroscopy. Both cyclic and linear peptides are reported, and the genetic organization of the NRPS modules within the biosynthetic gene cluster accounts for the observed structural diversity.

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Figures

Figure 1
Figure 1
The chemical structure of dentigerumycin B – D.
Figure 2
Figure 2
Gene map of the dentigerumycin BGC in Streptomyces sp. M41. The multimodular NRPSs that build the dentigerumycins are highlighted in blue and red, and the amino acid specificity of the adenylation domains are listed. One hypothesis regarding the production of 1 and 2 is that the growing nonribosomal peptide is intercepted by at least one of the four genes annotated as thioesterases (green), or a fifth belonging to the same enzyme superfamily, the α/β-hydrolases (orange), before reaching the final NRPS (blue).

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