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. 2018 Sep 28;8:14537. doi: 10.1038/s41598-018-32618-5

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© The Author(s) 2018

Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.

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Biosynthesis of 1 in Sphaerospermopsis sp. LEGE 00249. (A) The sphaerocyclamide (sph) biosynthetic gene cluster is organized in a bidirectional operon. Genes marked in green encode conserved and hypothetical proteins that have no recognized or predicted function; the SphE precursor peptide is marked in dark blue. The genes encoding cyanobactin proteases are marked in light blue. The prenyltransferase gene is marked in light grey and genes commonly found in cyanobactin gene clusters but without predicted function are shown in dark grey. A transposase is present between sphE and sphF genes. Cyanobactin precursor peptides encode hypervariable amino acid core sequences. The precursor peptide core that originates 1 is shown below the sphE gene. (B) Comparison of the extracted ion chromatograms ([M + H]⁺, 1) of methanol extracts of Sphaerospermopsis sp. LEGE 00249 (bottom), E. coli (pC6_00249) (top) and E. coli (pC1_00249) (middle, negative control) and comparison of MS² data from m/z 919 ions (corresponding to 1, [M + H]⁺) obtained from the Sphaerospermopsis sp. LEGE 00249 extract (bottom) and from E. coli (pC6_00249) (top).