bis(1-[(1R,2S,3S,4R,5S,6S)-3-carbamimidamido-6-{[(2R,3R,4R,5S)-3-{[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy}-2,4,5-trihydroxycyclohexyl]guanidine); tris(sulfuric acid)

• ChemBase ID: 130846
• Molecular Formular: C42H84N14O36S3
• Molecular Mass: 1457.38356
• Monoisotopic Mass: 1456.43347808
• SMILES: C[C@H]1[C@@]([C@H]([C@@H](O1)O[C@H]1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1O)O)NC(=N)N)O)NC(=N)N)O[C@H]1[C@H]([C@@H]([C@H]([C@@H](O1)CO)O)O)NC)(C=O)O.C[C@H]1[C@@]([C@H]([C@@H](O1)O[C@H]1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1O)O)NC(=N)N)O)NC(=N)N)O[C@H]1[C@H]([C@@H]([C@H]([C@@H](O1)CO)O)O)NC)(C=O)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O
• Canonical SMILES: OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O.OC[C@@H]1O[C@@H](O[C@H]2[C@H](O[C@@H]3[C@@H](O)[C@H](O)[C@H]([C@@H]([C@H]3NC(=N)N)O)NC(=N)N)O[C@H]([C@]2(O)C=O)C)[C@H]([C@@H]([C@H]1O)O)NC.OC[C@@H]1O[C@@H](O[C@H]2[C@H](O[C@@H]3[C@@H](O)[C@H](O)[C@H]([C@@H]([C@H]3NC(=N)N)O)NC(=N)N)O[C@H]([C@]2(O)C=O)C)[C@H]([C@@H]([C@H]1O)O)NC
• InChI: InChI=1S/2C21H39N7O12.3H2O4S/c2*1-5-21(36,4-30)16(40-17-9(26-2)13(34)10(31)6(3-29)38-17)18(37-5)39-15-8(28-20(24)25)11(32)7(27-19(22)23)12(33)14(15)35;3*1-5(2,3)4/h2*4-18,26,29,31-36H,3H2,1-2H3,(H4,22,23,27)(H4,24,25,28);3*(H2,1,2,3,4)/t2*5-,6-,7-,8+,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,21+;;;/m00.../s1
• InChIKey: QTENRWWVYAAPBI-YZTFXSNBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(1-[(1R,2S,3S,4R,5S,6S)-3-carbamimidamido-6-{[(2R,3R,4R,5S)-3-{[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy}-2,4,5-trihydroxycyclohexyl]guanidine); tris(sulfuric acid)
• IUPAC Traditional name: bis(1-[(1R,2S,3S,4R,5S,6S)-3-carbamimidamido-6-{[(2R,3R,4R,5S)-3-{[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy}-2,4,5-trihydroxycyclohexyl]guanidine); tris(sulfuric acid)
• Synonyms: Streptomycin solution; Streptomycin sulfate salt; Streptomycin sesquisulfate hydrate; Streptomycini sulfas; 链霉素 溶液; 链霉素 硫酸盐; 链霉素倍半硫酸盐; 硫酸链霉素

Database IDs

• CAS Number: 3810-74-0; 3810-74-0(anhydrous)
• EC Number: 223-286-0; 231-791-2
• MDL Number: MFCD00037023
• Beilstein Number: 3894995
• PubChem SID: 24899445; 24870421; 24899828; 24899705; 24899525; 24888475; 24899470; 162225124
• PubChem CID: 6419957

CALCULATED PROPERTIES

• Acid pKa: 10.877018
• H Acceptors: 19
• H Donor: 14
• LogD (pH = 5.5): -13.912841
• LogD (pH = 7.4): -12.161263
• Log P: -7.651423
• Molar Refractivity: 149.4707 cm^3
• Polarizability: 52.500404 Å^3
• Polar Surface Area: 331.43 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear
• Apperance: powder; white to off-white powder

Safety Information

• RTECS: WK4990000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; 63-22
• Safety Statements: 36/37
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302; H302-H361
• GHS Precautionary statements: P281
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves; Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ~95% (T)
• Concentration: ~1 mg/mL in 1 mM EDTA
• Grade: analytical standard; Biotechnology Performance Certified; Ph Eur; VETRANAL™, analytical standard
• Potency: ≥720 I.U. per mg; ≥720 I.U. per mg (dried basis)
• Suitability: cell culture tested; plant cell culture tested; suitable for cell culture; suitable for mouse embryo cell culture
• Impurities: endotoxin, tested
• Sterility: γ-irradiated
• Loss on Drying: ≤5% loss on drying
• Mol. Weight: calculated mol wt 1457.38 ((C21H39N7O12)2 ?3H2O4S)
• Linear Formula: C21H39N7O12 · 1.5 H2SO4
• Empirical Formula (Hill Notation): C21H39N7O12 · 1.5H2O4S · xH2O; C21H39N7O12 · 1.5H2SO4

DETAILS

Sigma Aldrich - S0774

Application
Used together with penicillin and other agents to inhibit bacterial contamination in cell culture applications.
Biochem/physiol Actions
Mode of Action: Inhibits prokaryote protein synthesis. Binds to S12 protein of 30S ribosomal subunit, preventing the transition from initiation complex to chain-elongating ribosome, causing miscoding or inhibiting initiation. Mode of Resistance: Mutation in rpsL (gene for S12 ribosomal protein) prevents binding of streptomycin to ribosome. Aminoglycoside phosphotransferase also inactivates.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - S1277

Biochem/physiol Actions
Mode of Action: Inhibits prokaryote protein synthesis. Binds to S12 protein of 30S ribosomal subunit, preventing the transition from initiation complex to chain-elongating ribosome, causing miscoding or inhibiting initiation. Mode of Resistance: Mutation in rpsL (gene for S12 ribosomal protein) prevents binding of streptomycin to ribosome. Aminoglycoside phosphotransferase also inactivates.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Application
Recommended for use in embryo culture at 50 mg/L. Stock solutions should be sterile-filtered and stored at 2-8 °C for up to a month or at -20 °C for extended periods. Solutions are stable at 37 °C for 3 days. Use to inhibit bacterial protein synthesis at the level of initiation. Use to study mechanisms of streptomycin resistance. Use together with penicillin and other agents to inhibit bacterial contamination in cell culture applications.

Sigma Aldrich - S1567

Biochem/physiol Actions
Mode of Action: Inhibits prokaryote protein synthesis. Binds to S12 protein of 30S ribosomal subunit, preventing the transition from initiation complex to chain-elongating ribosome, causing miscoding or inhibiting initiation. Mode of Resistance: Mutation in rpsL (gene for S12 ribosomal protein) prevents binding of streptomycin to ribosome. Aminoglycoside phosphotransferase also inactivates.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.

Sigma Aldrich - S9137

Application
建议以 100mg/L 的量用于细胞培养应用。储存液应经过无菌过滤，在 2-8°C 下保存最多一个月或在 -20°C 下长期保存。溶液在 37°C 下可稳定 3 天。
Biochem/physiol Actions
Mode of Action: Inhibits prokaryote protein synthesis. Binds to S12 protein of 30S ribosomal subunit, preventing the transition from initiation complex to chain-elongating ribosome, causing miscoding or inhibiting initiation. Mode of Resistance: Mutation in rpsL (gene for S12 ribosomal protein) prevents binding of streptomycin to ribosome. Aminoglycoside phosphotransferase also inactivates.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - 46754

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - S6501

Application
Used to inhibit bacterial protein synthesis at the level of initiation inhibition.
Biochem/physiol Actions
Mode of Action: Inhibits prokaryote protein synthesis. Binds to S12 protein of 30S ribosomal subunit, preventing the transition from initiation complex to chain-elongating ribosome, causing miscoding or inhibiting initiation. Mode of Resistance: Mutation in rpsL (gene for S12 ribosomal protein) prevents binding of streptomycin to ribosome. Aminoglycoside phosphotransferase also inactivates.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.

Sigma Aldrich - 85880

Biochem/physiol Actions
Mode of Action: Inhibits prokaryote protein synthesis. Binds to S12 protein of 30S ribosomal subunit, preventing the transition from initiation complex to chain-elongating ribosome, causing miscoding or inhibiting initiation. Mode of Resistance: Mutation in rpsL (gene for S12 ribosomal protein) prevents binding of streptomycin to ribosome. Aminoglycoside phosphotransferase also inactivates.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Other Notes
Inhibits initiation and causes misreading of mRNA in protein synthesis1; Removal of DNA in cloning and expression of avidin in E. coli2.

Sigma Aldrich - 85884

Application
Used together with penicillin and other agents to inhibit bacterial contamination in cell culture applications.
Biochem/physiol Actions
Mode of Action: Inhibits prokaryote protein synthesis. Binds to S12 protein of 30S ribosomal subunit, preventing the transition from initiation complex to chain-elongating ribosome, causing miscoding or inhibiting initiation. Mode of Resistance: Mutation in rpsL (gene for S12 ribosomal protein) prevents binding of streptomycin to ribosome. Aminoglycoside phosphotransferase also inactivates.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.

Sigma Aldrich - S2522

Application
建议以 25-50μg/ml 的量用于分子生物学应用。
Biochem/physiol Actions
Mode of Action: Inhibits prokaryote protein synthesis. Binds to S12 protein of 30S ribosomal subunit, preventing the transition from initiation complex to chain-elongating ribosome, causing miscoding or inhibiting initiation. Mode of Resistance: Mutation in rpsL (gene for S12 ribosomal protein) prevents binding of streptomycin to ribosome. Aminoglycoside phosphotransferase also inactivates.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Reconstitution
直接在样品瓶中用无菌水 (25-20mg/ml) 制备储存液。储存液应在 -20°C 下保存。在 37°C 下可稳定 3 天。