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94675

Sigma-Aldrich

Valinomycin

≥99.0% (TLC)

Synonym(s):
Cyclo(L-Val-D-HyIva-D-Val-L-Lac-)3: HyIva = α-Hydroxyisovaleric acid, Lac = Lactic acid
Empirical Formula (Hill Notation):
C54H90N6O18
CAS Number:
Molecular Weight:
1111.32
Beilstein:
78657
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Quality Level

assay

≥99.0% (TLC)

form

powder

mp

187-190 °C

antibiotic activity spectrum

mycobacteria

Mode of action

cell membrane | interferes

storage temp.

2-8°C

SMILES string

CC(C)[C@@H]1NC(=O)[C@H](C)OC(=O)[C@@H](NC(=O)[C@H](OC(=O)[C@@H](NC(=O)[C@H](C)OC(=O)[C@H](NC(=O)[C@H](OC(=O)[C@@H](NC(=O)[C@H](C)OC(=O)[C@H](NC(=O)[C@H](OC1=O)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C

InChI

1S/C54H90N6O18/c1-22(2)34-49(67)73-31(19)43(61)55-38(26(9)10)53(71)77-41(29(15)16)47(65)59-36(24(5)6)51(69)75-33(21)45(63)57-39(27(11)12)54(72)78-42(30(17)18)48(66)60-35(23(3)4)50(68)74-32(20)44(62)56-37(25(7)8)52(70)76-40(28(13)14)46(64)58-34/h22-42H,1-21H3,(H,55,61)(H,56,62)(H,57,63)(H,58,64)(H,59,65)(H,60,66)/t31-,32-,33-,34-,35+,36+,37-,38-,39-,40+,41+,42+/m0/s1

InChI key

FCFNRCROJUBPLU-RPUZOQEISA-N

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General description

Valinomycin is a neutral cyclic dodecadepsipeptide antibiotic, that has a 36-member ring.
Chemical structure: peptide

Application

Valinomycin has been used as an internal standard in the cytotoxicity assay for the detection of cereulide produced by emetic Bacillus cereus. It has also been used in the measurement of the electrogenicity of bile salt/H+ antiport in Escherichia coli.

Biochem/physiol Actions

Valinomycin affects the ion transport behavior of mitochondrial systems.
K+-selective ionophoric cyclodepsipeptide; potassium ionophore which uncouples oxidative phosphorylation, induces apoptosis in murine thymocytes, inhibits NGF-induced neuronal differentiation and antagonizes ET-induced vasoconstriction.

Other Notes

Review

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 1 Oral

Storage Class Code

6.1B - Non-combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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More Documents

Quotes and Ordering

The molecular structure and some transport properties of valinomycin
Pinkerton M, et al.
Biochemical and Biophysical Research Communications, 35(4), 512-518 (1969)
Transmembrane voltage sensor
Membrane Science and Technology, 7, 847-886 (2003)
Measurement of the Electrogenicity of Bile Salt/H+ Antiport in Escherichia coli
Holdsworth S R and Law C J
Molecular Microbiology (2014)
Cytotoxicity assay for detection of cereulide produced by emetic Bacillus cereus
Frenzel E and Ehling-Schulz M
Molecular Microbiology (2012)
Crystal structure of valinomycin potassium picrate: anion effects on valinomycin cation complexes
Hamilton J A, et al.
Journal of the American Chemical Society, 103(19), 5880-5885 (1981)

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