Gentamicin C1a Pentaacetate Salt

• CAT Number: R007662
• CAS Number: 26098-04-4
• Molecular Formula: C19H39N5O7
• Molecular Weight: 449.549
• 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-(aminomethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol
• InChI: InChI=1S/C19H39N5O7/c1-19(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/h8-18,24-27H,3-7,20-23H2,1-2H3/t8-,9+,10-,11+,12-,13+,14+,15-,16+,17+,18+,19-/m0/s1
• InChIKey: VEGXETMJINRLTH-BOZYPMBZSA-N
• SMILES: CC1(COC(C(C1NC)O)OC2C(CC(C(C2O)OC3C(CCC(O3)CN)N)N)N)O

Gentamicin C1a sulfate is one of several components of the gentamicin C complex. Gentamicin C1a can comprise 10-35% 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 C1a differs from gentamicin C1 by a methyl group in the 6’ position of the purpurosamine (2-amino-hexose) ring. Gentamicin C1a sulfate, is ≥95.0% gentamicin C1a.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.