ArticleAngewandte Chemie (International ed. in English)2015
Biosynthesis-assisted structural elucidation of the bartolosides, chlorinated aromatic glycolipids from cyanobacteria.
Article in Angewandte Chemie (International ed. in English), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 30 papers.
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Who cites it
30 citing papers in PubMed, 59 citations in OpenAlex.
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- Halogenation-Guided Chemical Screening Uncovers Cyanobacterin Analogues from the CyanobacteriumJournal of natural products · 2025Article
- The Cyanobacterial Oxadiazine Nocuolin A Shows Broad-Spectrum Toxicity Against Protozoans and the Nematode C. elegans.Microbial ecology · 2025Article
- Chemical diversity of cyanobacterial natural products.Natural product reports · 2025Review
- Expanding the Diversity of the Cyanobacterial Dialkylresorcinol Bartoloside Family.Journal of natural products · 2024Article
- Incorporation and modification of fatty acids in cyanobacterial natural products biosynthesis.Chemical communications (Cambridge, England) · 2023Review
- Incorporation, fate, and turnover of free fatty acids in cyanobacteria.FEMS microbiology reviews · 2023Review
- Effects of Temperature, pH, and NaCl Concentration on Biomass and Bioactive Compound Production byLife (Basel, Switzerland) · 2023Article
- Structural Investigation of Aaptourinamine by a Novel Module-Assembly-Based Calculation.Marine drugs · 2022Article
- Marine Cyanobacteria as Sources of Lead Anticancer Compounds: A Review of Families of Metabolites with Cytotoxic, Antiproliferative, and Antineoplastic Effects.Molecules (Basel, Switzerland) · 2022Review
- Structural basis for an unprecedented enzymatic alkylation in cylindrocyclophane biosynthesis.eLife · 2022Article
- Cryptic halogenation reactions in natural product biosynthesis.Natural product reports · 2021Review
- Article
- Discovery of Cyanobacterial Natural Products Containing Fatty Acid Residues*.Angewandte Chemie (International ed. in English) · 2021Article
- Biosynthesis of Chlorinated Lactylates inJournal of natural products · 2021Article
- Halogenation-Guided Chemical Screening Provides Insight into Tjipanazole Biosynthesis by the Cyanobacterium Fischerella ambigua.Chembiochem : a European journal of chemical biology · 2020Article
- BrtB is an O-alkylating enzyme that generates fatty acid-bartoloside esters.Nature communications · 2020Article
- Diagnostically analyzingRSC advances · 2020Article
- Chemistry, bioactivity and biosynthesis of cyanobacterial alkylresorcinols.Natural product reports · 2019Review
- Chlorophyll Derivatives from Marine Cyanobacteria with Lipid-Reducing Activities.Marine drugs · 2019Article
Corrections and comments
- Erratum issued
Authors and funding
8 authors at 4 institutions in 2 countries.
Funding
Abstract
The isolation of the bartolosides, unprecedented cyanobacterial glycolipids featuring aliphatic chains with chlorine substituents and C-glycosyl moieties, is reported. Their chlorinated dialkylresorcinol (DAR) core presented a major structural-elucidation challenge. To overcome this, we discovered the bartoloside (brt) biosynthetic gene cluster and linked it to the natural products through in vitro characterization of the DAR-forming ketosynthase and aromatase. Bioinformatic analysis also revealed a novel potential halogenase. Knowledge of the bartoloside biosynthesis constrained the DAR core structure by defining key pathway intermediates, ultimately allowing us to determine the full structures of the bartolosides. This work illustrates the power of genomics to enable the use of biosynthetic information for structure elucidation.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.