(2R,3R,4R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; (2R,3R,4R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-[(1R)-1-(methylamino)ethyl]oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; (2R,3R,4R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-[(1R)-1-aminoethyl]oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; sulfuric acid

• ChemBase ID: 130786
• Molecular Formular: C60H125N15O25S
• Molecular Mass: 1488.785
• Monoisotopic Mass: 1487.86917558
• SMILES: C[C@H]([C@@H]1CC[C@H]([C@H](O1)O[C@@H]1[C@H](C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@H](C(CO1)(C)O)NC)O)N)N)N)N.C[C@H]([C@@H]1CC[C@H]([C@H](O1)O[C@@H]1[C@H](C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@H](C(CO1)(C)O)NC)O)N)N)N)NC.CC1(CO[C@@H]([C@@H]([C@H]1NC)O)O[C@H]1[C@@H](C[C@@H]([C@H]([C@@H]1O)O[C@@H]1[C@@H](CC[C@H](O1)CN)N)N)N)O.OS(=O)(=O)O
• Canonical SMILES: OS(=O)(=O)O.CN[C@@H]1[C@@H](O)[C@H](OCC1(C)O)O[C@H]1[C@H](N)C[C@@H]([C@H]([C@@H]1O)O[C@H]1O[C@@H](CC[C@H]1N)[C@H](N)C)N.CN[C@@H]([C@@H]1CC[C@H]([C@H](O1)O[C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@H]1OCC([C@@H]([C@H]1O)NC)(C)O)N)N)C.NC[C@@H]1CC[C@H]([C@H](O1)O[C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@H]1OCC([C@@H]([C@H]1O)NC)(C)O)N)N
• InChI: InChI=1S/C21H43N5O7.C20H41N5O7.C19H39N5O7.H2O4S/c1-9(25-3)13-6-5-10(22)19(31-13)32-16-11(23)7-12(24)17(14(16)27)33-20-15(28)18(26-4)21(2,29)8-30-20;1-8(21)12-5-4-9(22)18(30-12)31-15-10(23)6-11(24)16(13(15)26)32-19-14(27)17(25-3)20(2,28)7-29-19;1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17;1-5(2,3)4/h9-20,25-29H,5-8,22-24H2,1-4H3;8-19,25-28H,4-7,21-24H2,1-3H3;8-18,24-27H,3-7,20-23H2,1-2H3;(H2,1,2,3,4)/t9-,10-,11+,12-,13+,14+,15-,16-,17+,18-,19-,20-,21?;8-,9-,10+,11-,12+,13+,14-,15-,16+,17-,18-,19-,20?;8-,9+,10-,11+,12-,13+,14+,15-,16+,17+,18+,19?;/m110./s1
• InChIKey: RDEIXVOBVLKYNT-UTRRJPTHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; (2R,3R,4R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-[(1R)-1-(methylamino)ethyl]oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; (2R,3R,4R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-[(1R)-1-aminoethyl]oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; sulfuric acid
• IUPAC Traditional name: (2R,3R,4R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; (2R,3R,4R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-[(1R)-1-(methylamino)ethyl]oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; (2R,3R,4R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-[(1R)-1-aminoethyl]oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; sulfuric acid
• Synonyms: Gentamicin sulfate from Micromonospora purpurea; Gentamicin sulfate salt; Gentamicin sulfate; Gentamicin solution; Garamycin; Gentiomycin C; Gentamicin sulfate salt; 庆大霉素 硫酸酯 来源于紫红小单孢菌; 庆大霉素 硫酸盐; 庆大霉素 C; 庆大霉素 硫酸盐; 正泰霉素; 庆大霉素 硫酸酯; 庆大霉素 溶液

Database IDs

• CAS Number: 1405-41-0
• EC Number: 215-778-9
• MDL Number: MFCD00270181
• PubChem SID: 162225064
• PubChem CID: 71308338

CALCULATED PROPERTIES

• Acid pKa: 12.549178
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -17.685123
• LogD (pH = 7.4): -11.792577
• Log P: -3.1371555
• Molar Refractivity: 118.0207 cm^3
• Polarizability: 49.566326 Å^3
• Polar Surface Area: 199.73 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear, very faintly yellow; H2O: soluble50 mg/mL (As a stock solution. Stock solutions should be stored at -20 °C.); H2O: soluble50 mg/mL (As stock solution, store at -20°C. Stable at 37°C for 5 days.)
• Apperance: liquid; powder
• Optical Rotation: [α]20/D +110±8°, c = 1% in H2O
• pH: 4.0-5.5 (0.1 g/mL in H2O)

Safety Information

• RTECS: LY2625000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2; nwg
• Risk Statements: 42/43
• Safety Statements: 22-36/37-45; 23-36/37-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H317-H334
• GHS Precautionary statements: P261-P280-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves; Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Concentration: 1 mg/mL in 1 mM EDTA; 10 mg/mL in deionized water; 50 mg/mL gentamicin; 50 mg/mL gentamicin (deionized water); 50 mg/mL in deionized water; 50 μg/mL in H2O ( is the recommended working concentration for eukaryotic cell culture)
• Grade: Biotechnology Performance Certified; for cell biology; Hybri-Max™
• Potency: ~600 μg Gentamicin per mg; ≥590 μg Gentamicin base per mg
• Suitability: in accordance for cell culture; meets EP, USP testing specifications; meets USP testing specifications; plant cell culture tested; suitable for cell culture; suitable for hybridoma
• Impurities: ≤10 EU/mL endotoxins (LAL test); ≤10% water; endotoxin, tested
• Sterility: sterile-filtered; γ-irradiated
• Shelf Life: 2 yr at 2-8 °C ( for sterile filtered solutions.)
• Quality Level: PREMIUM
• Quality: Prepared in tissue culture grade water.
• Mol. Weight: Mr 694-723
• Linear Formula: C19-21H39-43N5O7 · 2.5H2SO4

DETAILS

Sigma Aldrich - 48757

Application
Used as a selection agent (gentamicin-resistance gene) in molecular biology applications.
Biochem/physiol Actions
Mode of Action: Inhibits protein synthesis by binding to L6 protein of 50S ribosomal subunit. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria, and mycoplasma.

Sigma Aldrich - G4793

Application
Used as a selection agent (gentamicin-resistance gene) in molecular biology applications.
Biochem/physiol Actions
Mode of action: Gentamicin causes codon misreading by binding to the 30S ribosomal subunit, blocking the translocation of peptidyl-tRNA from the acceptor site to the donor site.1,2 The bactericidal effect of gentamicin on Pseudomonas aeruginosa is exerted by the binding of gentamicin to the outer membrane, where it displaces natural cations, destabilizes the membrane, and forms holes in the cell surface.3Antimicrobial spectrum: Gram-negative bacteria, Staphylococcus aureus and other Gram-positive bacteria
General description
Gentamicin sulfate is a broad spectrum antibiotic. It inhibits the growth of a wide variety of Gram-positive and Gram-negative microorganisms, including strains resistant to tetracycline, chloramphenicol, kanamycin, and colistin, particularly strains of Pseudomonas,Proteus, Staphylococcus, and Streptococcus. Gentamicin sulfate inhibits bacterial protein biosynthesis by binding to the 30S subunit of the ribosome.

Sigma Aldrich - 48760

Application
Used as a selection agent (gentamicin-resistance gene) in molecular biology applications.
Biochem/physiol Actions
Mode of Action: Inhibits protein synthesis by binding to L6 protein of 50S ribosomal subunit. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria, and mycoplasma.
Unit Definition
1 U corresponds to 1 μg of the USP gentamicin sulfate reference standard

Sigma Aldrich - G1272

Application
Recommended for use in cell culture applications at 5 ml/L and used as a selection agent (gentamicin-resistance gene) in molecular biology applications.
Biochem/physiol Actions
作用方式：通过结合到 50S 核糖体亚基的 L6 蛋白上抑制蛋白质的合成。 抗菌谱：革兰氏阴性菌、革兰氏阳性菌和支原体。
Caution
Stable at 37 °C for 5 days.
Other Notes
Formulated to contain 10 mg/ml gentamicin in deionized water.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - G6896

Biochem/physiol Actions
Mode of action: Gentamicin causes codon misreading by binding to the 30S ribosomal subunit, blocking the translocation of peptidyl-tRNA from the acceptor site to the donor site.1,2 The bactericidal effect of gentamicin on Pseudomonas aeruginosa is exerted by the binding of gentamicin to the outer membrane, where it displaces natural cations, destabilizes the membrane, and forms holes in the cell surface.3Antimicrobial spectrum: Gram-negative bacteria, Staphylococcus aureus and other Gram-positive bacteria
General description
Gentamicin sulfate is a broad spectrum antibiotic. It inhibits the growth of a wide variety of Gram-positive and Gram-negative microorganisms, including strains resistant to tetracycline, chloramphenicol, kanamycin, and colistin, particularly strains of Pseudomonas,Proteus, Staphylococcus, and Streptococcus. Gentamicin sulfate inhibits bacterial protein biosynthesis by binding to the 30S subunit of the ribosome.

Sigma Aldrich - G4918

Application
Used as a selection agent (gentamicin-resistance gene) in molecular biology applications.
Biochem/physiol Actions
Mode of action: Gentamicin causes codon misreading by binding to the 30S ribosomal subunit, blocking the translocation of peptidyl-tRNA from the acceptor site to the donor site.1,2 The bactericidal effect of gentamicin on Pseudomonas aeruginosa is exerted by the binding of gentamicin to the outer membrane, where it displaces natural cations, destabilizes the membrane, and forms holes in the cell surface.3Antimicrobial spectrum: Gram-negative bacteria, Staphylococcus aureus and other Gram-positive bacteria
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - G1522

Biochem/physiol Actions
作用方式：通过结合到 50S 核糖体亚基的 L6 蛋白上抑制蛋白质的合成。 抗菌谱：革兰氏阴性菌、革兰氏阳性菌和支原体。
法律信息
Hybri-Max 商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - G1264

Application
Recommended for use in cell culture applications at 50 mg/L
Used as a selection agent (gentamicin-resistance gene) in cell culture and molecular biology applications. Recommended for use in cell culture applications at 50 mg/L
Biochem/physiol Actions
Mode of action: Gentamicin causes codon misreading by binding to the 30S ribosomal subunit, blocking the translocation of peptidyl-tRNA from the acceptor site to the donor site.1,2 The bactericidal effect of gentamicin on Pseudomonas aeruginosa is exerted by the binding of gentamicin to the outer membrane, where it displaces natural cations, destabilizes the membrane, and forms holes in the cell surface.3Antimicrobial spectrum: Gram-negative bacteria, Staphylococcus aureus and other Gram-positive bacteria
General description
Gentamicin sulfate is a broad spectrum antibiotic that inhibits the growth of a wide variety of Gram-positive and Gram-negative microorganisms, including strains resistant to tetracycline, chloramphenicol, kanamycin, and colistin; particularly strains of Pseudomonas, Proteus, Staphylococcus, and Streptococcus. Gentamicin sulfate inhibits bacterial protein biosynthesis by binding to the 30S subunit of the ribosome.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - G3632

Application
Used as a selection agent (gentamicin-resistance gene) in molecular biology applications.
Biochem/physiol Actions
Mode of action: Gentamicin causes codon misreading by binding to the 30S ribosomal subunit, blocking the translocation of peptidyl-tRNA from the acceptor site to the donor site.1,2 The bactericidal effect of gentamicin on Pseudomonas aeruginosa is exerted by the binding of gentamicin to the outer membrane, where it displaces natural cations, destabilizes the membrane, and forms holes in the cell surface.3Antimicrobial spectrum: Gram-negative bacteria, Staphylococcus aureus and other Gram-positive bacteria

Sigma Aldrich - 48755

Biochem/physiol Actions
Mode of Action: Inhibits protein synthesis by binding to L6 protein of 50S ribosomal subunit. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria, and mycoplasma.
Preparation Note
sterile filtered

Sigma Aldrich - G1914

Application
Used as a selection agent (gentamicin-resistance gene) in molecular biology applications.
Biochem/physiol Actions
Mode of action: Gentamicin causes codon misreading by binding to the 30S ribosomal subunit, blocking the translocation of peptidyl-tRNA from the acceptor site to the donor site.1,2 The bactericidal effect of gentamicin on Pseudomonas aeruginosa is exerted by the binding of gentamicin to the outer membrane, where it displaces natural cations, destabilizes the membrane, and forms holes in the cell surface.3Antimicrobial spectrum: Gram-negative bacteria, Staphylococcus aureus and other Gram-positive bacteria

Sigma Aldrich - G8648

Application
建议以 10-15μg/ml 的量用于分子生物学应用。
Biochem/physiol Actions
Mode of action: Gentamicin causes codon misreading by binding to the 30S ribosomal subunit, blocking the translocation of peptidyl-tRNA from the acceptor site to the donor site.1,2 The bactericidal effect of gentamicin on Pseudomonas aeruginosa is exerted by the binding of gentamicin to the outer membrane, where it displaces natural cations, destabilizes the membrane, and forms holes in the cell surface.3Antimicrobial spectrum: Gram-negative bacteria, Staphylococcus aureus and other Gram-positive bacteria
Reconstitution
直接用无菌水 (5-20mg/ml) 在样品瓶中制备储存液。储存液应储存在 -20°C 下。在 37°C 下可稳定 5 天。

Sigma Aldrich - G1397

Application
Used as a selection agent (gentamicin-resistance gene) in molecular biology and cell culture applications. Recommended for use in cell culture applications at 1 ml/L.
Biochem/physiol Actions
作用方式：通过结合到 50S 核糖体亚基的 L6 蛋白上抑制蛋白质的合成。 抗菌谱：革兰氏阴性菌、革兰氏阳性菌和支原体。
Caution
Stable at 37°C for 5 days.
Other Notes
Formulated to contain 50 mg/ml gentamicin in deionized water.
General description
Gentamicin sulfate is a broad spectrum antibiotic. It inhibits the growth of a wide variety of Gram-positive and Gram-negative microorganisms, including strains resistant to tetracycline, chloramphenicol, kanamycin, and colistin, particularly strains of Pseudomonas,Proteus, Staphylococcus, and Streptococcus. Gentamicin sulfate inhibits bacterial protein biosynthesis by binding to the 30S subunit of the ribosome.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information