(2S)-2-amino-3-[(2-diazoacetyl)oxy]propanoic acid

• ChemBase ID: 104123
• Molecular Formular: C5H7N3O4
• Molecular Mass: 173.12678
• Monoisotopic Mass: 173.04365572
• SMILES: N[C@@H](COC(=O)C=[N+]=[N-])C(=O)O
• Canonical SMILES: [N-]=[N+]=CC(=O)OC[C@@H](C(=O)O)N
• InChI: 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
• InChIKey: MZZGOOYMKKIOOX-VKHMYHEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-[(2-diazoacetyl)oxy]propanoic acid
• IUPAC Traditional name: azaserine
• Synonyms: O-Diazoacetyl-L-serine; AZASERINE; Azaserine; O-重氮乙酰基-L-丝氨酸; 偶氮丝氨酸

Database IDs

• CAS Number: 115-02-6
• EC Number: 204-061-6
• MDL Number: MFCD00036802
• Beilstein Number: 1726602
• PubChem SID: 24890511; 24890830; 162091920
• PubChem CID: 5284344

CALCULATED PROPERTIES

• Acid pKa: 1.5548805
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -4.6218204
• LogD (pH = 7.4): -4.6607447
• Log P: -4.6000333
• Molar Refractivity: 34.7488 cm^3
• Polarizability: 14.308945 Å^3
• Polar Surface Area: 106.69 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL, clear, yellow
• Apperance: lyophilized powder
• Melting Point: 146-162°C
• Vapor Pressure: 1.53 x 10-10 mmHg at 25 °C.

Safety Information

• Storage Condition: 0°C, Protect from light
• RTECS: VT9625000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811; 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Australian Hazchem: 2X
• Risk Statements: 25-40; R:25-45
• Safety Statements: 53-36/37/39-45; S:28-36/37/39-45-53
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H351
• GHS Precautionary statements: P281-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 3
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥98% (TLC); ≥99.0% (TLC)
• Grade: Hybri-Max™
• Suitability: suitable for hybridoma
• Impurities: endotoxin, tested
• Sterility: γ-irradiated
• Empirical Formula (Hill Notation): C5H7N3O4

DETAILS

MP Biomedicals - 02154805

(O-Diazoacetyl-L-serine) Crystalline

Sigma Aldrich - A4142

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.1 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.2

Sigma Aldrich - A1164

Application
For use in hybridoma cell culture applications as a myeloma selection agent. Used to study inhibition of formylglycinamide ribonucleotide amidotransferase and PRPP amidotransferase.
Reconstitution
10mL 无菌细胞培养基可复原一小瓶本品。储备液足以制备 500mL 培养基。最终工作浓度：5.7μM 偶氮丝氨酸。
法律信息
Hybri-Max 商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 11430

Other Notes
Studies on the L-system amino acid transporter1; Inducer of micromelial limbs2