(2S)-2-amino-4-[butyl(imino)oxo-λ6-sulfanyl]butanoic acid

• ChemBase ID: 155147
• Molecular Formular: C8H18N2O3S
• Molecular Mass: 222.30512
• Monoisotopic Mass: 222.10381345
• SMILES: CCCCS(=N)(=O)CC[C@@H](C(=O)O)N
• Canonical SMILES: CCCCS(=O)(=N)CC[C@@H](C(=O)O)N
• InChI: InChI=1S/C8H18N2O3S/c1-2-3-5-14(10,13)6-4-7(9)8(11)12/h7,10H,2-6,9H2,1H3,(H,11,12)/t7-,14?/m0/s1
• InChIKey: KJQFBVYMGADDTQ-CVSPRKDYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-[butyl(imino)oxo-λ^6-sulfanyl]butanoic acid
• IUPAC Traditional name: (2S)-2-amino-4-[butyl(imino)oxo-λ^6-sulfanyl]butanoic acid
• Synonyms: L-BSO; L-Buthionine-sulfoximine; (2S)-2-Amino-4-(S-butylsulfonimidoyl)butanoic Acid; L-Buthionine Sulfoximine; NSC 326231; L-Buthionine-(S,R)-sulfoximine

Database IDs

• CAS Number: 83730-53-4
• MDL Number: MFCD00067000
• Beilstein Number: 2367136
• PubChem SID: 162249285; 24278263
• PubChem CID: 119565

CALCULATED PROPERTIES

• Acid pKa: 2.181531
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.9740744
• LogD (pH = 7.4): -2.9773746
• Log P: -2.9709322
• Molar Refractivity: 54.0074 cm^3
• Polarizability: 22.389696 Å^3
• Polar Surface Area: 104.24 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Aqueous Acid; H2O: soluble50 mg/mL, clear, colorless to faintly yellow; Water
• Apperance: White to Off-White Solid
• Melting Point: 212-214°C; 224-228 °C (dec.)
• Optical Rotation: [α]20/D +33±1°, c = 1% in 1 M HCl

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: EK7713440
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... GCLC(2729), GCLM(2730)

Product Information

• Purity: ≥96.0% (TLC); ≥97% (TLC)
• Empirical Formula (Hill Notation): C8H18N2O3S

DETAILS

Sigma Aldrich - B2515

Biochem/physiol Actions
Blocks cellular resistance to chemotherapy by inhibiting γ-glutamylcysteine synthetase, a key enzyme in glutathione biosynthesis.2 Used to induce experimental glutathione deficiency, to investigate roles of glutathione in cellular processes.1
Packaging
1, 5 g in poly bottle
500 mg in poly bottle
Application
Used to induce experimental glutathione deficiency, to investigate roles of glutathione in cellular processes.1

Sigma Aldrich - 19175

Biochem/physiol Actions
Blocks cellular resistance to chemotherapy by inhibiting γ-glutamylcysteine synthetase, a key enzyme in glutathione biosynthesis.2 Used to induce experimental glutathione deficiency, to investigate roles of glutathione in cellular processes.1
Other Notes
Potent specific inhibitor of γ-glutamylcysteine synthetase2
Application
Used to induce experimental glutathione deficiency, to investigate roles of glutathione in cellular processes.1

Toronto Research Chemicals - B690270

A potent and specific inhibitor of alpha-glutamylcysteine synthetase.

REFERENCES

• Griffith, O.W., et al.: J. Biol. Chem., 254, 16, 7558 (1979)
• Griffith, O.W., Methods in Enzymology, 77, 59 (1979)
• Slivka, A., et al.: J. of Neurochemistry, 50, 5, 1391 (1979)
• Du, D-L, et al.: Cancer Research, 50, 4038 (1979)
• Sandor, V., et al.: J. of