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. 2022 Aug 8;13:4619. doi: 10.1038/s41467-022-32016-6

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© The Author(s) 2022

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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Fig. 2 — a Left panel: Total ion chromatogram (m/z 300–2000) of cyanobacterial crude extract and blank. The retention times (RT = 4.5–5.5 min) of major Ahp-cyclodepsipeptides are highlighted. Right panel: Deconvoluted extracted ion chromatogram (m/z 25,233 ± 5) of alpha-chymotrypsin screened against the cyanobacterial crude extract under native MS conditions and negative control. Acetonitrile (ACN) concentration on column and post-column (including make-up) are shown as dashed lines. The ACN concentrations are given at the pump for a given time, and a ~ 2 min delay time between pump and column has to be taken into account. b Correlation molecular network of deconvoluted chymotrypsin and putatively new small molecule inhibitors binders by native MS (A larger version of the network with detailed precursor mass labels of all nodes is available in the supporting information Supplementary Fig. 3). c Upper left panel: Extracted ion chromatogram (m/z 1,186.6284–1,186.6522) of putative chymotrypsin-binder rivulariapeptolide 1185 at RT = 5.5 min. Middle and upper right panel: Multiple charged and deconvoluted MS spectra and extracted ion chromatogram (m/z 26,420 ± 5) of a putative chymotrypsin-binder complex. The mass difference between the putative chymotrypsin-binder complex (m/z 26,420 ± 5) and apo-chymotrypsin (25,233 ± 5) suggests a molecular weight of 1187 ± 5 Da for the putative chymotrypsin-binder rivulariapeptolide 1185. Lower left panel: Extracted ion chromatogram (m/z 1,156.5819–1,156.6051) of putative chymotrypsin-binder rivulariapeptolide 1185 at RT = 5.1 min. Middle and lower right panel: Multiple charged and deconvoluted MS spectra Extracted ion chromatogram (m/z 26,385 ± 5) of a putative chymotrypsin-binder complex. Mass difference between the putative chymotrypsin-binder complex (m/z 26,385 ± 5) and apo-chymotrypsin (25,233 ± 5) suggests a molecular weight of 1152 ± 5 Da for the putative chymotrypsin-binder rivulariapeptolide 1155. (A larger version of mass spectra is shown in the supporting information Supplementary Fig. 5).