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Merck

N8028

Sigma-Aldrich

Nikkomycin Z from Streptomyces tendae

≥90% (HPLC)

Synonym(e):

Neopolyoxin C, Nikkomycin Z

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About This Item

Empirische Formel (Hill-System):
C20H25N5O10
CAS-Nummer:
Molekulargewicht:
495.44
MDL-Nummer:
UNSPSC-Code:
51102829
PubChem Substanz-ID:
NACRES:
NA.85

Qualitätsniveau

Assay

≥90% (HPLC)

Form

powder

Löslichkeit

H2O: soluble 5 mg/mL

Wirkungsspektrum von Antibiotika

fungi

Wirkungsweise

cell wall synthesis | interferes
enzyme | inhibits

Lagertemp.

2-8°C

SMILES String

C[C@@H]([C@H](N)C(=O)N[C@H]([C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=CC(=O)NC2=O)C(O)=O)[C@H](O)c3ccc(O)cn3

InChI

1S/C20H25N5O10/c1-7(13(28)9-3-2-8(26)6-22-9)11(21)17(31)24-12(19(32)33)16-14(29)15(30)18(35-16)25-5-4-10(27)23-20(25)34/h2-7,11-16,18,26,28-30H,21H2,1H3,(H,24,31)(H,32,33)(H,23,27,34)/t7-,11-,12+,13-,14-,15+,16+,18+/m0/s1

InChIKey

WWJFFVUVFNBJTN-JKEIIPFCSA-N

Allgemeine Beschreibung

Chemical structure: peptidyl nucleoside

Anwendung

Nikkomycin Z is used as a selective competitive inhibitor of chitin synthetase 3 in studies on fungal cell wall development. It is a potential treatment for human Encephalitozoon hellem, a microsporidian species and is used to study the changes of chitin and β--glucan under Nikkomycin Z exposure.

Biochem./physiol. Wirkung

Nikkomycin Z inhibits chitin synthase from converting UDP-GlcNAc into cell wall chitin due to its structural resemblance to UDP-N-acetylglucosamine.

Sonstige Hinweise

Keep container tightly closed in a dry and well-ventilated place.Keep in a dry place.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves


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L Popolo et al.
Journal of bacteriology, 179(2), 463-469 (1997-01-01)
The GGP1/GAS1 gene codes for a glycosylphosphatidylinositol-anchored plasma membrane glycoprotein of Saccharomyces cerevisiae. The ggp1delta mutant shows morphogenetic defects which suggest changes in the cell wall matrix. In this work, we have investigated cell wall glucan levels and the increase
T Chapman et al.
Antimicrobial agents and chemotherapy, 36(9), 1909-1914 (1992-09-01)
An N-acetyl-D-[14C]glucosamine radiolabel incorporation assay has been used to monitor chitin biosynthesis in whole cells of Candida albicans both in vitro and in vivo in two different mouse infection models, one using the peritoneal cavity as a chamber in which
E Bigliardi et al.
Antimicrobial agents and chemotherapy, 44(11), 3012-3016 (2000-10-19)
Since 1985 microsporidia have been recognized as a cause of emerging infections in humans, mainly in immunocompromised human immunodeficiency virus-positive subjects. As chitin is a basic component of the microsporidian infective stage, the spore, we evaluated in vitro the susceptibility
H Decker et al.
Journal of general microbiology, 137(8), 1805-1813 (1991-08-01)
The structure-activity relationships of different nikkomycins were studied to evaluate the structural requirements for a potent chitin synthase inhibitor. We investigated the transport of the nikkomycins via the peptide transport system of the yeast Yarrowia lipolytica and determined the kinetic
Preeti M Chaudhary et al.
Mini reviews in medicinal chemistry, 13(2), 222-236 (2012-04-20)
Increased risk of fungal diseases in immunocompromised patients, emerging fungal pathogens, limited repertoire of antifungal drugs and resistance development against the drugs demands for development of new and effective antifungal agents. With greater knowledge of fungal metabolism efforts are being

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