119-04-0 Usage
Description
NEOMYCIN B is a tetracyclic antibacterial agent derived from neomycin, being a glycoside ester of neamine and neobiosamine B. It is an aminoglycoside antibiotic with a chemical structure that contributes to its antimicrobial properties.
Uses
Used in Pharmaceutical Industry:
NEOMYCIN B is used as a topical medication for treating various bacterial infections. Its application reason is due to its broad-spectrum antimicrobial activity, which helps in controlling and preventing infections caused by both gram-positive and gram-negative bacteria.
Used in Preventive Medicine:
NEOMYCIN B is used as a preventive measure for hepatic encephalopathy and hypercholesterolemia. The application reason is its ability to reduce the risk of these conditions by managing the underlying factors and providing protection against potential complications.
Biochem/physiol Actions
Neomycin is an aminoglycoside antibiotic, produced by Streptomyces containing a minimum of 85% neomycin B. It acts as a selection agent for prokaryotic cells transformed using the neo selectable marker gene. Neomycin trisulfate is used to study the cytototoxic side effects of antibiotics, platelet-derived growth factor responses in certain fibroblasts and extraction of nuclear phosphatidylinositol 4,5-bisphosphate-interacting proteins. This product is recommended for use in cell culture applications at 5 mL/L.Mode of action: This product acts by binding to the 30S and 50S subunits, causing miscoding and inhibiting initiation and elongation during protein synthesis. Neomycin also blocks voltage-sensitive Ca2+ channels without affecting the Na+/Ca2+ antiporter in neurons.Antimicrobial spectrum: Neomycin acts against both gram-positive and gram-negative bacteria
Check Digit Verification of cas no
The CAS Registry Mumber 119-04-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 9 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 119-04:
(5*1)+(4*1)+(3*9)+(2*0)+(1*4)=40
40 % 10 = 0
So 119-04-0 is a valid CAS Registry Number.
InChI:InChI=1/C23H46N6O13/c24-2-7-13(32)15(34)10(28)21(37-7)40-18-6(27)1-5(26)12(31)20(18)42-23-17(36)19(9(4-30)39-23)41-22-11(29)16(35)14(33)8(3-25)38-22/h5-23,30-36H,1-4,24-29H2/t5-,6+,7-,8+,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+/m1/s1
119-04-0Relevant articles and documents
Characterization of a radical S-adenosyl-l-methionine epimerase, NeoN, in the last step of neomycin B biosynthesis
Kudo, Fumitaka,Hoshi, Shota,Kawashima, Taiki,Kamachi, Toshiaki,Eguchi, Tadashi
, p. 13909 - 13915 (2014)
The last step of neomycin biosynthesis is the epimerization at C-5 of neomycin C to give neomycin B. A candidate enzyme responsible for the epimerization was a putative radical S-adenosyl-l-methionine (SAM) enzyme, NeoN, which is uniquely encoded in the n
TOTAL SYNTHESIS OF NEOMYCIN B
Usui, Takayuki,Umezawa, Sumio
, p. 133 - 144 (2007/10/02)
Total synthesis of neomycin B, a pseudo-tetrasaccharide aminoglycoside antibiotic, has been achieved through two key glycosylation reactions.Coupling of 3-O-acetyl-2,6-diazido-4-O-benzyl-2,6-dideoxy-L-idopyranosyl chloride with 5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranose under modified Koenigs-Knorr conditions gave 70percent of the desired β-L disaccharide (3) and corresponding to neobiosamine in structure.After deisopropylidenation of 3 and acetylation, 1,2-di-O-acetyl-3-O-(3-O-acetyl-2,6-diazido-4-O-benzyl-2,6-dideoxy-β-L-idopyranosyl)-5-O-benzoyl-D-ribofuranose was coupled to HO-5 of 3,2',6'-tri-N-(benzyloxycarbonyl)-1-N:6-O-carbonyl-3',4'-di-O-(o-methoxybenzoyl)neamine, using trimethylsilyl trifluoromethanesulfonate, to give 60percent of the pseudo-tetrasaccharide 19 possessing the framework and masked functionality corresponding to neomycin B.Deblocking and reduction of the azido groups then gave neomycin B.