[The structure of antibiotic eremomycin B]
Bioorganicheskaia Khimiia
|November 26, 2009
Summary
A novel antibiotic, eremomycin B, was discovered from Amycolatopsis orientalis. This new compound differs from eremomycin by a unique N-carboxymethyl group on its eremosamine fragment.
Area of Science:
- Microbiology
- Natural Product Chemistry
- Organic Chemistry
Context:
- Amycolatopsis orientalis subsp. eremomycini is known to produce the antibiotic eremomycin.
- The isolation of novel antibiotic compounds is crucial for combating antimicrobial resistance.
- Structural elucidation of natural products provides insights into biosynthesis and potential applications.
Purpose:
- To isolate and characterize a new biologically active component from Amycolatopsis orientalis subsp. eremomycini.
- To determine the precise chemical structure of the novel antibiotic, eremomycin B.
- To identify the structural differences between eremomycin B and its known precursor, eremomycin.
Summary:
- A new antibiotic, designated eremomycin B, was successfully isolated from the culture filtrate of Amycolatopsis orientalis subsp. eremomycini.
- The molecular structure of eremomycin B was elucidated using advanced spectroscopic techniques, including Nuclear Magnetic Resonance (NMR) spectroscopy and mass spectrometry.
- Eremomycin B is structurally distinguished from eremomycin by the presence of an N-carboxymethyl substituent within its disaccharide eremosamine moiety.
Impact:
- The discovery of eremomycin B expands the repertoire of known antibiotics derived from microbial sources.
- Understanding the structural variations in antibiotics can guide the development of new antimicrobial agents.
- This finding contributes to the broader field of natural product drug discovery and development.
Related Concept Videos
Inhibitors of Bacterial Protein Synthesis
Aminoglycosides constitute a highly potent class of bactericidal antibiotics that exert their antimicrobial effects by targeting the bacterial ribosome, specifically disrupting protein synthesis. These polycationic molecules consist of amino-modified sugars linked via glycosidic bonds to an aminocyclitol core such as 2-deoxystreptamine or streptamine. Their strong positive charges facilitate tight binding to the negatively charged phosphate backbone of ribosomal RNA (rRNA), primarily at the 16S...
Inhibitors of Gram-positive Cell Wall Synthesis
Bacterial cell walls are typically rigid structures composed mainly of peptidoglycan, a mesh-like polymer that provides mechanical strength and maintains cell shape. The synthesis of peptidoglycan is a crucial process in bacterial growth and serves as a primary target for many antibiotics.Mechanism of Action of Beta-Lactam AntibioticsBeta-lactam antibiotics, such as penicillin, inhibit peptidoglycan synthesis in actively growing cells. These antibiotics share a characteristic four-membered...
Antifungal Agents
Amphotericin B is a broad-spectrum antifungal agent that exploits structural differences between fungal and mammalian cell membranes. Its amphipathic structure—featuring a hydrophobic polyene-lactone ring and a hydrophilic region containing mycosamine and carboxylic acid groups—enables selective binding to ergosterol, a sterol predominantly found in fungal plasma membranes. This selective interaction underlies the drug’s antifungal activity, although weak binding to cholesterol contributes to...
Production of Antibiotics
Penicillin, one of the earliest and most widely used antibiotics, is produced industrially by the filamentous fungus Penicillium chrysogenum. Large stirred-tank bioreactors ranging from tens to hundreds of thousands of liters maintain tightly controlled temperature, pH, and dissolved oxygen conditions to support fungal metabolism and maximize antibiotic yield. Penicillin is a secondary metabolite, synthesized primarily during the stationary growth phase, which requires a carefully managed...
Bacterial Cell Wall
The bacterial cell wall is an essential structural component that encases the plasma membrane, preserving cellular integrity, determining shape, and protecting against osmotic stress. This rigid yet flexible structure primarily comprises peptidoglycan, a polymer that forms a mesh-like matrix conferring mechanical strength and flexibility.Peptidoglycan Composition and StructurePeptidoglycan, the core of the bacterial cell wall, comprises alternating units of N-acetylglucosamine (NAG) and...
Factors Affecting Dissolution: Polymorphism, Amorphism and Pseudopolymorphism
Polymorphism refers to the existence of a drug substance in multiple crystalline forms, known as polymorphs. Recently, this term has been expanded to include solvates (forms containing a solvent), amorphous forms (non-crystalline forms), and desolvated solvates (forms from which the solvent has been removed).
Some polymorphic crystals possess lower aqueous solubility than their amorphous counterparts, leading to incomplete absorption. For instance, the oral suspension of Chloramphenicol, which...
Some polymorphic crystals possess lower aqueous solubility than their amorphous counterparts, leading to incomplete absorption. For instance, the oral suspension of Chloramphenicol, which...


