valinomycin
Sign in to saveAlso known as cyclo[-D-O-Val-D-Val-L-O-Ala-L-Val]3
Valinomycin is a naturally occurring dodecadepsipeptide used in the transport of potassium and as an antibiotic. Valinomycin is obtained from the cells of several Streptomyces species, S. fulvissimus being a notable one.
Research
4,445 papers- Valinomycin as a potential antiviral agent against coronaviruses: A review.Biomedical journal · 2020
- Cereulide and valinomycin, two important natural dodecadepsipeptides with ionophoretic activities.Polish journal of microbiology · 2010
- Theoretical investigation of hydroxylated analogues of valinomycin as potassium transporter.Computational biology and chemistry · 2023
- Nanoscale potassium sensing based on valinomycin-anchored fluorescent gold nanoclusters.Mikrochimica acta · 2024
- Polymorphic Forms of Valinomycin Investigated by NMR Crystallography.International journal of molecular sciences · 2020
via PubMed
Wikidata facts
- Mass
- 1110.63116
Show 4 more facts
- chemical formula
- C₅₄H₉₀N₆O₁₈
- canonical SMILES
- CC1C(=O)NC(C(=O)OC(C(=O)NC(C(=O)OC(C(=O)NC(C(=O)OC(C(=O)NC(C(=O)OC(C(=O)NC(C(=O)OC(C(=O)NC(C(=O)O1)C(C)C)C(C)C)C(C)C)C)C(C)C)C(C)C)C(C)C)C)C(C)C)C(C)C)C(C)C
- isomeric SMILES
- C[C@H]1C(=O)N[C@H](C(=O)O[C@@H](C(=O)N[C@@H](C(=O)O[C@H](C(=O)N[C@H](C(=O)O[C@@H](C(=O)N[C@@H](C(=O)O[C@H](C(=O)N[C@H](C(=O)O[C@@H](C(=O)N[C@@H](C(=O)O1)C(C)C)C(C)C)C(C)C)C)C(C)C)C(C)C)C(C)C)C)C(C)C)C(C)C)C(C)C
- Commons category
- Valinomycin
Sources (2)
via Wikidata · CC0
~4 min read
Article
4 sectionsContents
- Structure
- Applications
- References
- External links
Valinomycin is a naturally occurring dodecadepsipeptide used in the transport of potassium and as an antibiotic. Valinomycin is obtained from the cells of several Streptomyces species, S. fulvissimus being a notable one.
It is a member of the group of natural neutral ionophores because it does not have a residual charge. It consists of the enantiomers D- and L-valine (Val), , and L-lactic acid. Structures are alternately bound via amide and ester bridges. Valinomycin is highly selective for potassium ions over sodium ions within the cell membrane. It functions as a potassium-specific transporter and facilitates the movement of potassium ions through lipid membranes "down" the electrochemical potential gradient. The stability constant K for the potassium-valinomycin complex is nearly 100,000 times larger than that of the sodium-valinomycin complex. This difference is important for maintaining the selectivity of valinomycin for the transport of potassium ions (and not sodium ions) in biological systems.