A4142

Azaserine

≥98% (TLC)

• Synonym(s): O-Diazoacetyl-L-serine
• Empirical Formula (Hill Notation): C₅H₇N₃O₄
• CAS Number: 115-02-6
• Molecular Weight: 173.13
• UNSPSC Code: 12352209
• NACRES: NA.26
• PubChem Substance ID: 24890830
• EC Number: 204-061-6
• Beilstein/REAXYS Number: 1726602
• MDL number: MFCD00036802

Properties

• Quality Segment: 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

Description

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.

Safety Information

• Pictograms: GHS06,GHS08
• Signal Word: Danger
• Hazard Codes: H301,H351
• Precautionary Statements: P201 - P301 + P310 + P330
• 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: WGK 3
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable
• PPE (personal protective equipment): Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges