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Documenti fondamentali

74155

Sigma-Aldrich

Nonactin

from Streptomyces sp., ≥97.0% (TLC)

Sinonimo/i:

Ammonium ionophore

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About This Item

Formula empirica (notazione di Hill):
C40H64O12
Numero CAS:
Peso molecolare:
736.93
Beilstein:
76434
Numero CE:
Codice UNSPSC:
51102829
ID PubChem:
NACRES:
NA.85

Origine biologica

Streptomyces sp.

Livello qualitativo

Saggio

≥97.0% (TLC)

Stato

powder

Colore

white to faint yellow

Spettro attività antibiotica

Gram-positive bacteria

Modalità d’azione

DNA synthesis | interferes
cell membrane | interferes
enzyme | inhibits

Temperatura di conservazione

2-8°C

Stringa SMILE

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-
RMIXHJPMNBXMBU-QIIXEHPYSA-N

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Descrizione generale

Chemical structure: macrolide
May contain the homologues monactin and dinactin

Applicazioni

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) .

Azioni biochim/fisiol

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 .

Confezionamento

5 mg

Altre note

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

Codice della classe di stoccaggio

13 - Non Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

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)
S Krasne et al.
Science (New York, N.Y.), 174(4007), 412-415 (1971-10-22)
An abrupt loss of effectiveness of the presumed carriers, nonactin and valinomycin, in mediating ion conductance occurred at the same temperature as the membrane fluidity, judged visually, was lost. By contrast, the effects of the presumed channel-former, gramicidin, were the
Svetlana S Efimova et al.
Langmuir : the ACS journal of surfaces and colloids, 28(26), 9908-9914 (2012-06-19)
The effects of various subclasses of flavonoids, Rose Bengal, and different styrylpyridinium dyes on the magnitude of the dipole potential of membranes composed of pure phospholipids and sterol-containing bilayers were investigated. Changes in the steady-state membrane conductance induced by cation-ionophore
Peter Jani et al.
Biotechnology journal, 3(2), 202-208 (2007-12-08)
The optimization of the biosynthetic pathways is highly attractive for the large-scale preparation of macrotetrolides, because overall yields in the chemical synthesis of compounds like nonactin have been very low. A key success factor determining the outcome of such optimizations

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