Total Synthesis and Biological Assessment of Novel Albicidins Discovered by Mass Spectrometric Networking
Open accessAbstract
Natural products represent an important source of potential novel antimicrobial drug leads. Low production by microorganisms in cell culture often delays the structural elucidation or even prevents a timely discovery. Starting from the anti‐Gram‐negative antibacterial compound albicidin produced by Xanthomonas albilineans, we describe a bioactivity‐guided approach combined with non‐targeted tandem mass spectrometry and spectral (molecular) networking for the discovery of novel antimicrobial compounds. We report eight new natural albicidin derivatives, four of which bear a β‐methoxy cyanoalanine or β‐methoxy asparagine as the central α‐amino acid. We present the total synthesis of these albicidins, which facilitated the unambiguous determination of the (2 S,3 R)‐stereoconfiguration which is complemented by the assessment of the stereochemistry on antibacterial activity.
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Bioactivity-based molecular networking approaches have been successful in guiding the isolation of novel compounds with specific activity, such as antibacterial or antiviral activity.
“These approaches have been successful in guiding the isolation of novel compounds with specific activity (e.g., antibacterial or antiviral).”
From Connecting metabolome and phenotype: recent advances in functional metabolomics tools for the identification of bioactive natural products (2024) · cites this paper as [51]
The paper reports discovering eight new albicidin derivatives using a bioactivity-guided molecular networking approach (p. 2). Its workflow selected fractions with antibacterial activity (Communication, p. 3). This supports the antibacterial example, but our copy does not report antiviral activity or an antiviral discovery. (LLM, conf=0.86)
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References 26 · Cited by 36
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- Authors
- von Eckardstein, L., Petras, D., Dang, T., Cociancich, S., Sabri, S., Grätz, S., Kerwat, D., Seidel, M., Pesic, A., Dorrestein, P. C., Royer, M., Weston, J. B., & Süssmuth, R. D.
- Affiliations
- Institut für Chemie Technische Unitersität Berlin Strasse des 17. Juni 124 10623 Berlin Germany
- University of California San Diego (US)
- Technische Universität Berlin (DE)
- Centre de Coopération Internationale en Recherche Agronomique pour le Développement (FR)
- Corresponding author
- Süssmuth, Roderich D.
- ORCID
- Venue
- Chemistry – A European Journal
- Publisher
- Wiley
- Published
- 2017-10-12
- Volume
- 23
- Issue
- 61
- Pages
- 15316-15321
- ISSN
- 0947-6539 (ISSN-L)
- 1521-3765
- OpenAlex
- W2752551171
- Cited by
- 36
- References
- 26
- Citations by year
- 2026: 1 · 2025: 2 · 2024: 3 · 2023: 2 · 2022: 2 · 2021: 10 · 2020: 3 · 2019: 8 · 2018: 5
- FWCI
- 3.06
- Type
- journal article
- Language
- en
- Open access
- green
- hal.science
- Licence
- Locations
- Chemistry - A European Journal (publishedVersion)
- PubMed (publishedVersion)
- HAL (submittedVersion, cc-by-sa)
- Agritrop (Cirad) (submittedVersion)
- Funders
- Bundesministerium für Bildung und Forschung (VDI 03VP00030)
- Deutsche Forschungsgemeinschaft (SU 239/11-1, SU 239/18-1, PE 2600/1-1)
- Agence Nationale de la Recherche (ANR-09-BLANC-0413-01)
- Topics
- Health Sciences › Medicine › Pharmacology › Microbial Natural Products and Biosynthesis
- Physical Sciences › Chemistry › Organic Chemistry › Advanced Synthetic Organic Chemistry
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Chemical Synthesis and Analysis
- Keywords
- albicidin, total synthesis, Xanthomonas albilineans, antimicrobial natural products, stereochemistry, antibacterial activity, tandem mass spectrometry, Gram-negative bacteria
- MeSH terms
- Anti-Bacterial Agents, Biological Products, Chromatography, High Pressure Liquid, Gram-Negative Bacteria, Gram-Positive Bacteria, Microbial Sensitivity Tests, Organic Chemicals, Stereoisomerism, Structure-Activity Relationship, Xanthomonas, Tandem Mass Spectrometry
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