Gentamicin C2a sulfate

• CAT Number: R000532
• CAS Number: 59751-72-3
• Molecular Formula: C20H41N5O7
• Molecular Weight: 463.576
• Purity: ≥95%
• Storage: -20°C
• IUPAC Name: (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-[(1S)-1-aminoethyl]oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol
• InChI: InChI=1S/C20H41N5O7/c1-8(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/h8-19,25-28H,4-7,21-24H2,1-3H3/t8-,9+,10-,11+,12-,13-,14+,15+,16-,17+,18+,19+,20-/m0/s1
• InChIKey: XUFIWSHGXVLULG-BSBKYKEKSA-N
• SMILES: CC(C1CCC(C(O1)OC2C(CC(C(C2O)OC3C(C(C(CO3)(C)O)NC)O)N)N)N)N

Gentamicin C2a sulfate is one of three components of the gentamicin C complex and can comprise 25-55% gentamicin depending on the manufacturer or manufacturing process. The gentamicin C complex comprises approximately 80% gentamicin and exhibits the most potent antimicrobial activity. The higher antimicrobial activity of the group C gentamicins is thought to arise from the lack of hydroxy groups on the 3’ and 4’ positions of the purpurosamine (2-amino-hexose) fragments. Gentamicin C2 and C2a are both stereoisomers. Gentamicin C2a is ≥95.0% gentamicin C2a.Aminoglycosides target the 30S ribosomal subunit resulting in an inability to read mRNA ultimately producing a faulty or nonexistent protein.

Reference

Davis, Bernard D. /Mechanism of Bactericidal Action of Aminoglycosides./Microbiological Reviews 51.3 (1987): 341-50.Sarna, Katarzyna, and Agata Blazewicz. /Determination of Gentamicin Sulphate Composition and Related Substances in Pharmaceutical Preparations by LC with Charged Aerosol Detection./ PubMed (2010)Vydrin, A. F. /Component Composition of Gentamicin Sulfate Preparations./ Pharmaceutical Chemistry Journal 37.8 (2003): 448-49. Web. 15 Oct. 2013.Weinstein, Marvin J. /Biological Activity of the Antibiotic Components of the Gentamicin Complex./ Journal of Bacteriology 94.3 (1967): 789-90. Web. 15 Oct. 2013.