ArticleChemistry & biology2015
In vivo biosynthesis of terpene nucleosides provides unique chemical markers of Mycobacterium tuberculosis infection.
Article in Chemistry & biology, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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Who cites it
24 citing papers in PubMed, 47 citations in OpenAlex.
- The Evolutionary History and Modern Diversity of Triterpenoid Cyclases.Molecular biology and evolution · 2025Article
- The evolutionary history and modern diversity of triterpenoid cyclases.bioRxiv : the preprint server for biology · 2025Article
- Unraveling Mycobacterium tuberculosis acid resistance and pH homeostasis mechanisms.FEBS letters · 2025Review
- Mycobacteria that cause tuberculosis have retained ancestrally acquired genes for the biosynthesis of chemically diverse terpene nucleosides.PLoS biology · 2024Article
- Sulphides from garlic essential oil dose-dependently change the distribution of glycerophospholipids and induce N6-tuberculosinyladenosine formation in mycobacterial cells.Scientific reports · 2023Article
- Mycobacterium tuberculosis and its clever approaches to escape the deadly macrophage.World journal of microbiology & biotechnology · 2023Review
- Actinomycetes as Producers of Biologically Active Terpenoids: Current Trends and Patents.Pharmaceuticals (Basel, Switzerland) · 2023Review
- The fat is in the lysosome: how Mycobacterium tuberculosis tricks macrophages into storing lipids.The Journal of clinical investigation · 2023Article
- A terpene nucleoside from M. tuberculosis induces lysosomal lipid storage in foamy macrophages.The Journal of clinical investigation · 2023Article
- Investigation of Acid-Base Catalysis in Halimadienyl Diphosphate Synthase Involved inACS bio & med chem Au · 2022Article
- Chemical Synthesis of Cell Wall Constituents ofChemical reviews · 2021Review
- Aptamer-Based Diagnostic Systems for the Rapid Screening of TB at the Point-of-Care.Diagnostics (Basel, Switzerland) · 2021Review
- Bacterial terpenome.Natural product reports · 2021Review
- Article
- Article
- Antibacterial Natural Halimanes: Potential Source of Novel Antibiofilm Agents.Molecules (Basel, Switzerland) · 2020Review
- Arginine in the FARM and SARM: A Role in Chain-Length Determination for Arginine in the Aspartate-Rich Motifs of Isoprenyl Diphosphate Synthases fromMolecules (Basel, Switzerland) · 2018Article
- Semisynthesis, Characterization and Evaluation of New Adenosine Derivatives as Antiproliferative Agents.Molecules (Basel, Switzerland) · 2018Article
- T cell autoreactivity directed toward CD1c itself rather than toward carried self lipids.Nature immunology · 2018Article
- Fluorination of Naturally Occurring N⁶-Benzyladenosine Remarkably Increased Its Antiviral Activity and Selectivity.Molecules (Basel, Switzerland) · 2017Article
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16 authors at 7 institutions in 4 countries.
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Abstract
Although small molecules shed from pathogens are widely used to diagnose infection, such tests have not been widely implemented for tuberculosis. Here we show that the recently identified compound, 1-tuberculosinyladenosine (1-TbAd), accumulates to comprise >1% of all Mycobacterium tuberculosis lipid. In vitro and in vivo, two isomers of TbAd were detected that might serve as infection markers. Using mass spectrometry and nuclear magnetic resonance, we established the structure of the previously unknown molecule, N(6)-tuberculosinyladenosine (N(6)-TbAd). Its biosynthesis involves enzymatic production of 1-TbAd by Rv3378c followed by conversion to N(6)-TbAd via the Dimroth rearrangement. Intact biosynthetic genes are observed only within M. tuberculosis complex bacteria, and TbAd was not detected among other medically important pathogens, environmental bacteria, and vaccine strains. With no substantially similar known molecules in nature, the discovery and in vivo detection of two abundant terpene nucleosides support their development as specific diagnostic markers of tuberculosis.
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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.