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A4142

Sigma-Aldrich

Azaserine

≥98% (TLC)

Synonyma:

O-Diazoacetyl-L-serine

Přihlásitk zobrazení cen stanovených pro organizaci a smluvních cen
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About This Item

Empirický vzorec (Hillův zápis):
C5H7N3O4
Číslo CAS:
115-02-6
Molekulová hmotnost:
173.13
Beilstein/REAXYS Number:
1726602
EC Number:
204-061-6
MDL number:
MFCD00036802
UNSPSC Code:
12352209
PubChem Substance ID:
24890830
NACRES:
NA.26

Quality Level

100

assay

≥98% (TLC)

form

powder

color

off-white to yellow-green

antibiotic activity spectrum

fungi

mode of action

enzyme | inhibits

storage temp.

−20°C

SMILES string

N[C@@H](COC(=O)C=[N+]=[N-])C(O)=O

InChI

1S/C5H7N3O4/c6-3(5(10)11)2-12-4(9)1-8-7/h1,3H,2,6H2,(H,10,11)/t3-/m0/s1

InChI key

MZZGOOYMKKIOOX-VKHMYHEASA-N

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Související kategorie

General description

Chemical structure: amino acid derivatives

Application

Used in cell culture for the selection of HGPRT revertants.

Biochem/physiol Actions

Azaserine is an antibiotic and antifungal; it may also act as a tumor inducer. It is a structural analog of glutamine and competes with glutamine in binding to enzymes involved in purine biosynthesis. Azaserine inhibits purine biosynthesis by covalently reacting with cysteine residues in the enzyme active sites, such as in formylglycinamide ribonucleotide amidotransferase and PRPP amidotransferase. Azaserine can induce DNA damage via the formation of carboxymethylated bases and O6-methylguanine. Secretion of exo-1,3-β-glucanase and germ-tube formation of Candida albicans were inhibited by azaserine.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

hcodes

H301,H351

Hazard Classifications

Acute Tox. 3 Oral - Carc. 2

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Osvědčení o analýze (COA)

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Sigma-Aldrich

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Sigma-Aldrich

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Sigma-Aldrich

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Formaldehyde solution

Kornberg, A., and Baker, T.
DNA Replication, 57-60 (1992)
S P Ram et al.
Journal of general microbiology, 130(5), 1227-1236 (1984-05-01)
Exo-(1----3)-beta-glucanase, beta-glucosidase, autolysin and trehalase were assayed in situ in Candida albicans during yeast growth, starvation and germ-tube formation. Cell viability, germ-tube formation, intracellular glucose-6-phosphate dehydrogenase and beta-glucosidase were unaffected in cells incubated in 0.1 M-HC1 for 15 min at
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We hypothesized that under high glucose conditions, activation of the hexosamine pathway leads to impaired nitric oxide (NO)-dependent arteriolar dilation. Skeletal muscle arterioles (diameter: ~160μm) isolated from male Wistar rats were exposed to normal glucose (NG, 5.5mmol/L) or high glucose
Kei Wada et al.
Journal of molecular biology, 380(2), 361-372 (2008-06-17)
gamma-Glutamyltranspeptidase (GGT) catalyzes the cleavage of such gamma-glutamyl compounds as glutathione, and the transfer of their gamma-glutamyl group to water or to other amino acids and peptides. GGT is involved in a number of biological phenomena such as drug resistance
Céline Masclaux-Daubresse et al.
Plant physiology, 140(2), 444-456 (2006-01-13)
Glutamate (Glu) metabolism and amino acid translocation were investigated in the young and old leaves of tobacco (Nicotiana tabacum L. cv Xanthi) using [15N]ammonium and [2-15N]Glu tracers. Regardless of leaf age, [15N]ammonium assimilation occurred via glutamine synthetase (GS; EC 6.1.1.3)
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