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N8028

Sigma-Aldrich

Nikkomycin Z from Streptomyces tendae

≥90% (HPLC)

Synonym(s):

Neopolyoxin C, Nikkomycin Z

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About This Item

Empirical Formula (Hill Notation):
C20H25N5O10
CAS Number:
59456-70-1
Molecular Weight:
495.44
MDL number:
MFCD00869648
UNSPSC Code:
51102829
PubChem Substance ID:
24897849
NACRES:
NA.85
Pricing and availability is not currently available.

Quality Level

200

Assay

≥90% (HPLC)

form

powder

solubility

H2O: soluble 5 mg/mL

antibiotic activity spectrum

fungi

Mode of action

cell wall synthesis | interferes
enzyme | inhibits

storage temp.

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

InChI key

WWJFFVUVFNBJTN-JKEIIPFCSA-N

General description

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[1] and is used to study the changes of chitin and β--glucan under Nikkomycin Z exposure[2].

Biochem/physiol Actions

Nikkomycin Z inhibits chitin synthase from converting UDP-GlcNAc into cell wall chitin due to its structural resemblance to UDP-N-acetylglucosamine[3].

Other Notes

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000402991
0000389389
0000374443
0000402991
0000344445

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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
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
Jine Li et al.
Microbial cell factories, 11, 135-135 (2012-10-10)
Polyoxins are potent inhibitors of chitin synthetases in fungi and insects. The gene cluster responsible for biosynthesis of polyoxins has been cloned and sequenced from Streptomyces cacaoi and tens of polyoxin analogs have been identified already. The polyoxin biosynthetic gene
Jine Li et al.
Metabolic engineering, 13(3), 336-344 (2011-02-05)
Acting as competitive inhibitors of chitin synthase, nikkomycins and polyoxins are potent antibiotics against pathogenic fungi. Taking advantage of the structural similarities between these two peptidyl nucleoside antibiotics, genes required for the biosynthesis of the dipeptidyl moiety of polyoxin from
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