Bacillithiol is an antioxidant thiol produced in Bacilli

Glutathione is a nearly ubiquitous low-molecular-weight thiol and antioxidant, although it is conspicuously absent from most Gram-positive bacteria. We identify here the structure of bacillithiol, a novel and abundant thiol produced by Bacillus species, Staphylococcus aureus, and Deinococcus radiodurans. Bacillithiol is the α-anomeric glycoside of l-cysteinyl-d-glucosamine with l-malic acid and likely functions as an antioxidant. Bacillithiol, like structurally similar mycothiol, may serve as a substitute for glutathione.

• Publication year

  2009

• Venue

  Nature Chemical Biology

• Publication date

  2009-07-05

• Fields of study

  Biology, Medicine, Chemistry

• Identifiers
  DOI 10.1038/nchembio.189PMID 19578333PMCID 3510479
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Proteomics

  2011cited by this paper
• Biosynthesis and Functions of Mycothiol, the Unique Protective Thiol of Actinobacteria

  2008cited by this paper
• Oxidant‐dependent switching between reversible and sacrificial oxidation pathways for Bacillus subtilis OhrR

  2008cited by this paper
• The role of thioredoxin TrxA in Bacillus subtilis: A proteomics and transcriptomics approach

  2008cited by this paper
• Pyridine nucleotide complexes with Bacillus anthracis coenzyme A-disulfide reductase: a structural analysis of dual NAD(P)H specificity.

  2008cited by this paper
• Mycothiol: synthesis, biosynthesis and biological functions of the major low molecular weight thiol in actinomycetes.

  2008cited by this paper
• A complex thiolate switch regulates the Bacillus subtilis organic peroxide sensor OhrR

  2007cited by this paper
• Structure of the type III pantothenate kinase from Bacillus anthracis at 2.0 A resolution: implications for coenzyme A-dependent redox biology.

  2007cited by this paper
• Mycothiol-dependent proteins in actinomycetes.

  2007cited by this paper
• IL-13受体α2降低血吸虫病肉芽肿的炎症反应并延长宿主存活时间[英]/Mentink-Kane MM,Cheever AW，Thompson RW，et al//Proc Natl Acad Sci U S A

  2005cited by this paper
• Activity-guided identification of (S)-malic acid 1-O-D-glucopyranoside (morelid) and gamma-aminobutyric acid as contributors to umami taste and mouth-drying oral sensation of morel mushrooms (Morchella deliciosa Fr.).

  2005cited by this paper
• Role of a Cysteine Synthase in Staphylococcus aureus

  2004cited by this paper
• Expression, purification, and characterization of Mycobacterium tuberculosis mycothione reductase.

  1999cited by this paper
• Coenzyme A Disulfide Reductase, the Primary Low Molecular Weight Disulfide Reductase from Staphylococcus aureus

  1998cited by this paper
• Staphylococcus aureus Coenzyme A Disulfide Reductase, a New Subfamily of Pyridine Nucleotide-Disulfide Oxidoreductase

  1998cited by this paper
• The structure of U17 isolated from Streptomyces clavuligerus and its properties as an antioxidant thiol.

  1995cited by this paper
• Mechanisms for the oxygen radical-mediated toxicity of various thiol-containing compounds in cultured mammalian cells.

  1994cited by this paper
• Evolution of glutathione metabolism.

  1991cited by this paper
• Isolation and characterization of 2-O-β-d-Glucopyranosyl-l-malic acid from Synadenium pereskiifolium

  1990cited by this paper
• Glutathione : chemical, biochemical, and medical aspects

  1989cited by this paper
• Thioredoxin.

  1985cited by this paper
• Functions of Glutathione: Biochemical, Physiological, Toxicological, and Clinical Aspects

  1983cited by this paper
• Genetics of the alpha-ketoglutarate dehydrogenase complex of Bacillus subtilis

  1978cited by this paper
• Occurrence of glutathione in bacteria

  1978cited by this paper

• Couple action of some proteases from feather keratin-degrading bacterium B.licheniformis CP-16.

  2026cites this paper
• Breaking the Bonds of Aging: The Underappreciated Roles of Aberrant Cysteine Crosslinks and Protective Thiol Interventions.

  2026cites this paper
• Disarming bacterial iron homeostasis and sulfur antioxidant defenses via coordination-driven photosensitizer de-aggregation for enhanced photodynamic infection eradication.

  2026cites this paper
• Effects of N-Acetyl Cysteine on Human Post-Thaw Sperm Quality and Mitochondrial Uncoupling Protein 2 Relative Quantity

  2025cites this paper
• Ammonium depletion induces changes in low molecular weight thiol levels in Escherichia coli and Bacillus subtilis

  2025influential citation
• Disulfiram induces redox imbalance and perturbations in central glucose catabolism and metal homeostasis to inhibit the growth of Staphylococcus aureus

  2025influential citation
• Molecular Engineering to Construct the High-Performance Activatable Near-infrared-II Fluorogenic Sensor for In Vivo Glutathione Imaging and Its Clinical Application

  2025cites this paper
• The methyltransferase NmbA methylates the low-molecular weight thiol bacillithiol, and displays a specific structural architecture

  2025cites this paper
• Differential reactivity of bacillithiol, mycothiol and glutathione with nitroxyl (HNO): Structural determinants and potential biological implications

  2025cites this paper
• Bacillus spp. Antibacterial Activity Induced by Triphenyl Tetrazolium Chloride against Ralstonia solanacearum: Oxidative Stress Response and Metabolome Changes.

  2025cites this paper
• Reduction of Pentavalent Vanadium via Enhanced Levels of Sulfhydryl by Elemental Sulfur Reducing Bacteria from a Stone Coal Mining Region

  2025cites this paper
• N-Organothio β-Lactams Offer New Opportunities for Controlling Pathogenic Bacteria

  2025cites this paper
• The Genetic Determinants of Extreme UV Radiation and Desiccation Tolerance in a Bacterium Recovered from the Stratosphere

  2025cites this paper
• Glutathione S-Transferase Mediated Epoxide Conversion: Functional and Structural Properties of an Enantioselective Catalyst

  2025cites this paper
• Reductive activation of the disulfide-containing antibiotic thiolutin is mediated by both bacillithiol and FAD-dependent disulfide reductases

  2025cites this paper
• Complex effects of a prescribed burn on a prairie soil bacterial community

  2025cites this paper
• Bacillus subtilis Response to Mercury Toxicity: A Defense Mediated by Sulphur-Rich Molecules and Oxidative Prevention Systems

  2025cites this paper
• Aminopeptidase M17 in bacteria: insights into structure, function, and potential as a drug target

  2025cites this paper
• Antibacterial properties of reduced graphene oxide fibers fabricated by hydrothermal method

  2024cites this paper
• Liquid Phase Electron Microscopy of Bacterial Ultrastructure

  2024cites this paper
• Transcription factor AbrB regulates ROS generation and clearance in Bacillus licheniformis.

  2024cites this paper
• A granular view of the traits controlling soil bacterial community reconstruction following a prescribed burn

  2024cites this paper
• Pattern-based rapid and robust profiling of gut microbiota and its metabolism with a single fluorescent probe

  2024cites this paper
• Low-molecular-weight thiol transferases in redox regulation and antioxidant defence

  2024cites this paper
• The crystal structure of mycothiol disulfide reductase (Mtr) provides mechanistic insight into the specific low-molecular-weight thiol reductase activity of Actinobacteria

  2024cites this paper
• The bacillithiol pathway is required for biofilm formation in Staphylococcus aureus.

  2024cites this paper
• Stress-Induced Sulfide Production by Bacillus subtilis and Bacillus megaterium

  2024cites this paper
• A new ROS response factor YvmB protects Bacillus licheniformis against oxidative stress under adverse environment

  2024cites this paper
• Sulfinamide Formation from the Reaction of Bacillithiol and Nitroxyl.

  2023cites this paper
• Diverse roles of low-molecular weight thiol GSH in Francisella’s virulence, location sensing and GSH-stealing from host

  2023cites this paper
• Emerging roles of low-molecular-weight thiols at the host-microbe interface.

  2023cites this paper
• Bacillus subtilis YtpP and Thioredoxin A Are New Players in the Coenzyme-A-Mediated Defense Mechanism against Cellular Stress

  2023cites this paper
• “Graphene nanospikes exert bactericidal effect through mechanical damage and oxidative stress”

  2023cites this paper
• Bacterial metabolism and susceptibility to cell wall-active antibiotics.

  2023cites this paper
• Comparison of the structure and activity of thioredoxin 2 and thioredoxin 1 from Acinetobacter baumannii

  2023cites this paper
• Antioxidant defense of Deinococcus radiodurans: how does it contribute to extreme radiation resistance?

  2023influential citation
• MerA functions as a hypothiocyanous acid reductase and defense mechanism in Staphylococcus aureus

  2023cites this paper
• Unique alcohol dehydrogenases involved in algal sugar utilization by marine bacteria

  2023cites this paper
• The genome of Bacillus tequilensis EA-CB0015 sheds light into its epiphytic lifestyle and potential as a biocontrol agent

  2023cites this paper
• Streptococcus pyogenes Hijacks Host Glutathione for Growth and Innate Immune Evasion

  2022influential citation
• Bioresponsive nano-antibacterials for H2S-sensitized hyperthermia and immunomodulation against refractory implant–related infections

  2022cites this paper
• Bacterial metalo-aminopeptidases as targets in human infectious diseases.

  2022cites this paper
• Isolation and characterization of a highly effective bacterium Bacillus cereus b-525k for hexavalent chromium detoxification

  2022cites this paper
• Pharmacological evaluation of disulfiram analogs as antimicrobial agents and their application as inhibitors of fosB-mediated fosfomycin resistance

  2022cites this paper
• Thiol Reductases in Deinococcus Bacteria and Roles in Stress Tolerance

  2022cites this paper
• Oxidation of bacillithiol during killing of Staphylococcus aureus USA300 inside neutrophil phagosomes

  2022cites this paper
• Unravelling Formaldehyde Metabolism in Bacteria: Road towards Synthetic Methylotrophy

  2022influential citation
• Specific Features of the Proteomic Response of Thermophilic Bacterium Geobacillus icigianus to Terahertz Irradiation

  2022influential citation
• Reversible Redox-Dependent Conformational Switch of the C-Terminal α-Helical Lid of Human Hsp70 Observed by In-Cell NMR.

  2022cites this paper
• Glyoxalase 2: Towards a Broader View of the Second Player of the Glyoxalase System

  2022cites this paper
• Acute Toxicity of Divalent Mercury to Bacteria Explained by the Formation of Dicysteinate and Tetracysteinate Complexes Bound to Proteins in Escherichia coli and Bacillus subtilis.

  2021cites this paper
• Underground metabolism facilitates the evolution of novel pathways for vitamin B6 biosynthesis

  2021cites this paper
• The Bacillus subtilis monothiol bacilliredoxin BrxC (YtxJ) and the Bdr (YpdA) disulfide reductase reduce S-bacillithiolated proteins

  2021cites this paper
• Bacterial Approaches for Assembling Iron-Sulfur Proteins

  2021influential citation
• The glutathione import system satisfies the Staphylococcus aureus nutrient sulfur requirement and promotes interspecies competition

  2021cites this paper
• Influence of Redox Imbalances on the Transposition of Insertion Sequences in Deinococcus geothermalis

  2021cites this paper
• Using microbial metalo-aminopeptidases as targets in human infectious diseases

  2021cites this paper
• Structural and Biochemical Characterization of Thioredoxin-2 from Deinococcus radiodurans

  2021cites this paper
• New roles for glutathione: Modulators of bacterial virulence and pathogenesis

  2021cites this paper
• Dietary thiols accelerate aging of C. elegans

  2021cites this paper
• Newly synthesized palladium(II) complexes with aminothiazole derivatives: in vitro study of antimicrobial activity and antitumor activity on the human prostate cancer cell line.

  2021cites this paper
• Atypical Bacilliredoxin AbxC Plays a Role in Responding to Oxidative Stress in Radiation-Resistant Bacterium Deinococcus radiodurans

  2021cites this paper
• Ten-Year Retrospective of the Vanderbilt Institute of Chemical Biology Chemical Synthesis Core.

  2021cites this paper
• Glutathione utilization protects Streptococcus pneumoniae against lactoperoxidase-derived hypothiocyanous acid.

  2021cites this paper
• The Functions of Thioredoxin 1 in Neurodegeneration

  2021cites this paper
• Glutathione and Polyamines in Bacteria

  2021cites this paper
• The Writers, Readers, and Erasers in Redox Regulation of GAPDH

  2020cites this paper
• Thiol-based redox switches in the major pathogen Staphylococcus aureus

  2020cites this paper
• Structure elucidation of the redox cofactor mycofactocin reveals oligo-glycosylation by MftF

  2020cites this paper
• The Crystal Structures of Bacillithiol Disulfide Reductase Bdr (YpdA) Provide Structural and Functional Insight into a New Type of FAD-Containing NADPH-Dependent Oxidoreductase

  2020cites this paper
• Redox Regulation by Protein S-Glutathionylation: From Molecular Mechanisms to Implications in Health and Disease

  2020cites this paper
• Effects of Boiling Time on the Antioxidant Activity of Moringa Leaf Extract

  2020cites this paper
• Antioxidants

  2020cites this paper
• Antioxidant effects of N‐acetylcysteine on the male reproductive system: A systematic review

  2020cites this paper
• Mechanism of resistance focusing on copper, mercury and arsenic in extremophilic organisms, how acidophiles and thermophiles cope with these metals

  2020cites this paper
• Staphylococcus aureus glucose-induced biofilm accessory protein A (GbaA) is a monothiol-dependent electrophile sensor.

  2020cites this paper
• Crystal structure of the AhpD-like protein DR1765 from Deinococcus radiodurans R1.

  2020cites this paper
• Redox and Thiols in Archaea

  2020cites this paper
• Role of Glutathione in Buffering Excess Intracellular Copper in Streptococcus pyogenes

  2020cites this paper
• Role of Pseudomonas aeruginosa Glutathione Biosynthesis in Lung and Soft Tissue Infection

  2020cites this paper
• Copper Coordination Compounds as Biologically Active Agents

  2020cites this paper
• The Crystal Structures of Bacillithiol Disulfide Reductase YpdA Reveal Structural and Functional Insight into a New Type of FAD-Containing NADPH-Dependent Oxidoreductases

  2020cites this paper
• N-methyl-bacillithiol, a Novel Thiol from Anaerobic Bacteria

  2019cites this paper
• YpdA, a putative bacillithiol disulfide reductase, contributes to cellular redox homeostasis and virulence in Staphylococcus aureus

  2019cites this paper
• Cytosolic Copper Binding by a Bacterial Storage Protein and Interplay with Copper Efflux

  2019cites this paper
• Characterization of synergistic antibacterial effect of silver nanoparticles and ebselen

  2019cites this paper
• Coenzyme A: a protective thiol in bacterial antioxidant defence.

  2019cites this paper
• Exposure of Pseudomonas aeruginosa to bactericidal hypochlorous acid during neutrophil phagocytosis is compromised in cystic fibrosis

  2019cites this paper
• Crystal structure of DinB/YfiT protein DR0053 from D. radiodurans R1

  2019cites this paper
• Crystal structure of the highly radiation-inducible DinB/YfiT superfamily protein DR0053 from Deinococcus radiodurans R1.

  2019cites this paper
• The role of thiols in antioxidant systems.

  2019cites this paper
• Superoxide Dismutase and Pseudocatalase Increase Tolerance to Hg(II) in Thermus thermophilus HB27 by Maintaining the Reduced Bacillithiol Pool

  2019cites this paper
• Thiol-producing microbiota of the intestine modulate oxidative stress and inflammation in Chronic Kidney Disease

  2019cites this paper
• Evaluation of effects of selenium nanoparticles on Bacillus subtilis

  2019cites this paper
• Mass spectrometric studies of Cu(I)-binding to the N-terminal domains of B. subtilis CopA and influence of bacillithiol.

  2019cites this paper
• Mycobacterium smegmatis moxifloxacin persister cells produce high levels of hydroxyl radical, generating genetic resisters selectable not only with moxifloxacin, but also with ethambutol and isoniazid.

  2019cites this paper
• Antimicrobial garlic-derived diallyl polysulfanes: Interactions with biological thiols in Bacillus subtilis.

  2019cites this paper
• The Disulfide Stress Response and Protein S-thioallylation Caused by Allicin and Diallyl Polysulfanes in Bacillus subtilis as Revealed by Transcriptomics and Proteomics

  2019cites this paper
• Challenges and Opportunities for Small-Molecule Fluorescent Probes in Redox Biology Applications

  2018cites this paper
• The effect of sulfur-containing amino acids on the biosynthesis of lincomycin

  2018cites this paper