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N8028

Sigma-Aldrich

Nikkomycin Z from Streptomyces tendae

≥90% (HPLC)

Synonyme(s) :

Neopolyoxin C, Nikkomycin Z

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About This Item

Formule empirique (notation de Hill):
C20H25N5O10
Numéro CAS:
59456-70-1
Poids moléculaire :
495.44
Numéro MDL:
MFCD00869648
Code UNSPSC :
51102829
ID de substance PubChem :
24897849
Nomenclature NACRES :
NA.85

Niveau de qualité

200

Pureté

≥90% (HPLC)

Forme

powder

Solubilité

H2O: soluble 5 mg/mL

Spectre d'activité de l'antibiotique

fungi

Mode d’action

cell wall synthesis | interferes
enzyme | inhibits

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

WWJFFVUVFNBJTN-JKEIIPFCSA-N

Description générale

Chemical structure: peptidyl nucleoside

Application

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.

Actions biochimiques/physiologiques

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

Autres remarques

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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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
Matthew M Draelos et al.
Nature chemical biology, 17(2), 213-221 (2020-12-02)
Kinases are annotated in many nucleoside biosynthetic gene clusters but generally are considered responsible only for self-resistance. Here, we report an unexpected 2'-phosphorylation of nucleoside biosynthetic intermediates in the nikkomycin and polyoxin pathways. This phosphorylation is a unique cryptic modification
Taiga Miyazaki et al.
FEMS yeast research, 10(3), 343-352 (2010-03-11)
The Slt2 mitogen-activated protein kinase pathway plays a major role in maintaining fungal cell wall integrity. In this study, we investigated the effects of SLT2 deletion and overexpression on drug susceptibility and virulence in the opportunistic fungal pathogen Candida glabrata.
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