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MilliporeSigma

74155

Sigma-Aldrich

Nonactin

from Streptomyces sp., ≥97.0% (TLC)

Sinónimos:

Ammonium ionophore

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About This Item

Fórmula empírica (notación de Hill):
C40H64O12
Número de CAS:
Peso molecular:
736.93
Beilstein/REAXYS Number:
76434
EC Number:
UNSPSC Code:
51102829
PubChem Substance ID:
NACRES:
NA.85

biological source

Streptomyces sp.

Quality Level

assay

≥97.0% (TLC)

form

powder

color

white to faint yellow

antibiotic activity spectrum

Gram-positive bacteria

mode of action

DNA synthesis | interferes
cell membrane | interferes
enzyme | inhibits

storage temp.

2-8°C

SMILES string

C[C@H]1C[C@@H]2CC[C@@H](O2)[C@@H](C)C(=O)O[C@H](C)C[C@H]3CC[C@H](O3)[C@H](C)C(=O)O[C@@H](C)C[C@@H]4CC[C@@H](O4)[C@@H](C)C(=O)O[C@H](C)C[C@H]5CC[C@H](O5)[C@H](C)C(=O)O1

InChI

1S/C40H64O12/c1-21-17-29-9-13-34(49-29)26(6)38(42)46-23(3)19-31-11-15-36(51-31)28(8)40(44)48-24(4)20-32-12-16-35(52-32)27(7)39(43)47-22(2)18-30-10-14-33(50-30)25(5)37(41)45-21/h21-36H,9-20H2,1-8H3/t21-,22+,23+,24-,25-,26+,27+,28-,29-,30+,31+,32-,33-,34+,35+,36-

InChI key

RMIXHJPMNBXMBU-QIIXEHPYSA-N

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General description

Chemical structure: macrolide
May contain the homologues monactin and dinactin

Application

Nonactin is used as a neutral lipid membrane soluble ammonium (and potassium) ionophore, as an uncoupler of oxidative phosphorylation, and to inhibit surface expression of certain heat shock proteins (HSP60) [1][2].

Biochem/physiol Actions

Nonactin is a macrotetrolide that forms complexes with alkali cations, such as potassium and sodium. Nonactin has been reported to inhibit the processing of cytoplasmic precursor proteins destined for the mitochondria. Nonactin is a uncoupler of oxidative phosphorylation [3].

Packaging

5 mg

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Store under inert gas.Moisturesensitive. Keep in a dry place.
Natural macrotetrolide

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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[Macrotetrolides].
W Keller-Schierlein et al.
Fortschritte der Chemie organischer Naturstoffe = Progress in the chemistry of organic natural products. Progres dans la chimie des substances organiques naturelles, 26, 161-189 (1968-01-01)
Total synthesis of nonactin.
Ju Y.L.; Byeang H.K.
Tetrahedron, 52, 571-571 (1996)
Sergey M Korotkov et al.
Journal of biochemical and molecular toxicology, 21(2), 81-91 (2007-04-12)
The effects of Tl(+) ions on isolated rat liver mitochondria were studied in the presence of nonactin, a cyclic ionophore. Nonenergized rat liver mitochondria were increasingly swollen at an elevated concentration of Tl(+) in the 160 mOsm medium containing 0-150
Joshua B Phillips et al.
Bioorganic & medicinal chemistry letters, 20(19), 5936-5938 (2010-08-31)
We have shown that the intentional engineering of a natural product biosynthesis pathway is a useful way to generate stereochemically complex scaffolds for use in the generation of combinatorial libraries that capture the structural features of both natural products and
Sarah B Luesse et al.
Bioorganic & medicinal chemistry letters, 18(14), 3946-3949 (2008-07-01)
The synthesis of a library of nonactic acid-derived triazoloamide derivatives and their evaluation as antimicrobial agents is described.

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