Merck, 94675-10MG, Valinomycin

Name: Valinomycin
Brand: Merck
SKU: 94675-10MG

Size:10 mg, Cyclo(L-Val-D-HyIva-D-Val-L-Lac-)₃: HyIva = α-Hydroxyisovaleric acid, Lac = Lactic acid, ≥99.0% (TLC)

Available Catalog Numbers

94675-100MG 94675-10MG 94675-500MG

Catalog Number: 94675-10MG

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Category

Antibiotics & Antimycotics

Pack Size10 mg

TagsChemistry & Biochemicals Biochemicals Antibiotics

CollectionsMerck Biochemicals Collection: Trusted Lab Reagents & Buffers Merck Cell Culture Supplements & Reagents: Complete Solutions for Research & Bioproduction Merck Roche Life Science Products for PCR, RT‑PCR & Nucleic Acid Purification

Description

General description
Chemical structure: peptide
Valinomycin is a neutral cyclic dodecadepsi-peptide antibiotic, that has a 36-member ring.Valinomycin consists of twelve stereogenic centers that are made of three repeating sequences of a tetramer of D-α-hydroxyisovalericacid-D-valine-L-lactate-L-valine. It shows antibacterial, antitumor, antifungal, antiviral, and insecticidal properties. Valinomycin exerts its antiviral activity against human coronavirus OC43 (HCoV-OC43), severe acute respiratory syndrome coronavirus (SARS-CoV), and middle-east respiratory syndrome coronavirus (MERS-CoV).
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
K⁺-selective ionophore which uncouples oxidative phosphorylation.
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.
Valinomycin affects the ion transport behavior of mitochondrial systems.

Specifications

General

Web Name Suffix Override	≥99.0% (TLC), K+ ionophore, powder
NACRES	NA.32
PubChem Substance ID	329770374
UNSPSC Code	12352200
EC Number	217-896-6
MDL number	MFCD00005114
Beilstein/REAXYS Number	78657
InChI key	FCFNRCROJUBPLU-RPUZOQEISA-N
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
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
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

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Merck, 94675-10MG, Valinomycin

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