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15 results on '"Stanišić, Aleksa"'

4. Total Synthesis and Functional Evaluation of IORs, Sulfonolipid‐based Inhibitors of Cell Differentiation inSalpingoeca rosetta

Author

Raguž, Luka, primary, Peng, Chia‐Chi, additional, Rutaganira, Florentine U. N., additional, Krüger, Thomas, additional, Stanišić, Aleksa, additional, Jautzus, Theresa, additional, Kries, Hajo, additional, Kniemeyer, Olaf, additional, Brakhage, Axel A., additional, King, Nicole, additional, and Beemelmanns, Christine, additional

Published
2022
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7. HAMA: a multiplexed LC-MS/MS assay for specificity profiling of adenylate-forming enzymes† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c9sc04222a

Author

Stanišić, Aleksa, Hüsken, Annika, and Kries, Hajo

Subjects
Chemistry, heterocyclic compounds
Abstract

Adenylation enzymes are engineering targets in ribosomal and nonribosomal peptide synthesis. Through multiplexed LC-MS/MS measurement of hydroxamates, the HAMA assay records specificity profiles of these enzymes in a snap., Adenylation enzymes selecting substrates for ribosomal and nonribosomal protein and peptide biosynthesis have been popular targets of enzyme engineering. Previous standard assays for adenylation specificity have been cumbersome and failed to reflect the competition conditions inside a cell because they measure substrates one at a time. We have developed an adenylation assay based on hydroxamate quenching and LC-MS/MS detection of hydroxamate products testing dozens of competing amino acid substrates in parallel. Streamlined specificity profiling of adenylation enzymes will facilitate engineering and directed evolution of ribosomal and nonribosomal peptide synthesis.

Published
2019

9. Total Synthesis and Functional Evaluation of IORs, Sulfonolipid‐based Inhibitors of Cell Differentiation in Salpingoeca rosetta.

Author

Raguž, Luka, Peng, Chia‐Chi, Rutaganira, Florentine U. N., Krüger, Thomas, Stanišić, Aleksa, Jautzus, Theresa, Kries, Hajo, Kniemeyer, Olaf, Brakhage, Axel A., King, Nicole, and Beemelmanns, Christine

Subjects
CELL differentiation, FLUORESCENT probes, TARTARIC acid, ACID derivatives, PROTEOMICS, SULFONIC acids
Abstract

The choanoflagellate Salpingoeca rosetta is an important model system to study the evolution of multicellularity. In this study we developed a new, modular, and scalable synthesis of sulfonolipid IOR‐1A (six steps, 27 % overall yield), which acts as bacterial inhibitor of rosette formation in S. rosetta. The synthesis features a decarboxylative cross‐coupling reaction of a sulfonic acid‐containing tartaric acid derivative with alkyl zinc reagents. Synthesis of 15 modified IOR‐1A derivatives, including fluorescent and photoaffinity‐based probes, allowed quantification of IOR‐1A, localization studies within S. rosetta cells, and evaluation of structure‐activity relations. In a proof of concept study, an inhibitory bifunctional probe was employed in proteomic profiling studies, which allowed to deduce binding partners in bacteria and S. rosetta. These results showcase the power of synthetic chemistry to decipher the biochemical basis of cell differentiation processes within S. rosetta. [ABSTRACT FROM AUTHOR]

Published
2022
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14. Sulfonium Acids Loaded onto an Unusual Thiotemplate Assembly Line Construct the Cyclopropanol Warhead of a Burkholderia Virulence Factor

Author

Trottmann, Felix, Ishida, Keishi, Franke, Jakob, Stanišić, Aleksa, Ishida-Ito, Mie, Kries, Hajo, Pohnert, Georg, Hertweck, Christian, Trottmann, Felix, Ishida, Keishi, Franke, Jakob, Stanišić, Aleksa, Ishida-Ito, Mie, Kries, Hajo, Pohnert, Georg, and Hertweck, Christian

Abstract

Pathogenic bacteria of the Burkholderia pseudomallei group cause severe infectious diseases such as glanders and melioidosis. Malleicyprols were identified as important bacterial virulence factors, yet the biosynthetic origin of their cyclopropanol warhead has remained enigmatic. By a combination of mutational analysis and metabolomics we found that sulfonium acids, dimethylsulfoniumpropionate (DMSP) and gonyol, known as osmolytes and as crucial components in the global organosulfur cycle, are key intermediates en route to the cyclopropanol unit. Functional genetics and in vitro analyses uncover a specialized pathway to DMSP involving a rare prokaryotic SET-domain methyltransferase for a cryptic methylation, and show that DMSP is loaded onto the NRPS-PKS hybrid assembly line by an adenylation domain dedicated to zwitterionic starter units. Then, the megasynthase transforms DMSP into gonyol, as demonstrated by heterologous pathway reconstitution in E. coli. © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

Published
2020

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