534-47-4

Basic information

• Product Name: paromamine
• Synonyms: paromamine;4-O-(2-Amino-2-deoxy-α-D-glucopyranosyl)-2-deoxy-D-streptamine;4-O-(2-Amino-2-deoxy-alpha-D-glucopyranosyl)-2-deoxy-D-streptamine;4-O-alpha-D-Glucosaminyl-2-deoxystreptamine;Gentamine A;Neomycin D
• CAS NO: 534-47-4
• Molecular Formula: C₁₂H₂₅N₃O₇
• Molecular Weight: 323.3428
• Mol File: 534-47-4.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 593.6°Cat760mmHg
• Flash Point: 312.8°C
• Appearance: /
• Density: 1.56g/cm³
• Vapor Pressure: 1.46E-16mmHg at 25°C
• Refractive Index: 1.651
• CAS DataBase Reference: paromamine(CAS DataBase Reference)
• NIST Chemistry Reference: paromamine(534-47-4)
• EPA Substance Registry System: paromamine(534-47-4)

Safety Data

• Hazardous Substances Data: 534-47-4(Hazardous Substances Data)

Usage

Description

Paromamine is an aminoglycoside antibiotic that is derived from the 4alpha,6alpha-diaminocyclohexane-1beta,2alpha,3beta-triol structure, with the pro-R hydroxy group converted to its 2-amino-alpha-D-glucoside derivative. It is known for its potent antimicrobial properties and is widely used in the treatment of various bacterial infections.

Uses

Used in Pharmaceutical Industry:
Paromamine is used as an antimicrobial agent for the treatment of bacterial infections, particularly those caused by gram-negative bacteria. It works by binding to the bacterial 30S ribosomal subunit, leading to misreading of the genetic code and subsequent inhibition of protein synthesis.
Used in Research and Development:
Paromamine is also utilized in research and development for the discovery of new antibiotics and the study of bacterial resistance mechanisms. Its unique structure and mode of action make it a valuable tool in the development of novel antimicrobial agents.
Used in Veterinary Medicine:
In addition to human medicine, paromamine is used as an antimicrobial agent in veterinary medicine for the treatment of bacterial infections in animals. Its broad-spectrum activity makes it effective against a wide range of bacterial pathogens.
Used in Drug Resistance Studies:
Paromamine is employed in studies aimed at understanding the mechanisms of drug resistance in bacteria. By examining the interactions between paromamine and bacterial cells, researchers can gain insights into the development of resistance and potentially develop strategies to combat it.

InChI:InChI=1/C12H25N3O7/c13-3-1-4(14)11(10(20)7(3)17)22-12-6(15)9(19)8(18)5(2-16)21-12/h3-12,16-20H,1-2,13-15H2/t3-,4+,5-,6-,7+,8-,9-,10-,11-,12-/m1/s1

Upstream product

• 6128-39-8 paromomycin hydrochloride 
• 7205-49-4 paromomycin sulfate 
• 7542-37-2 paromomycin 
• 2037-48-1 2-deoxystreptamine 
• 90852-19-0 (1α,2β,3α,4β,6β)-4,6-Diazido-1,2,3-cyclohexantriol-triacetat 
• 90899-14-2 (1α,2β,3α,4β,6β)-4,6-Diazido-1,2,3-cyclohexantriol 
• 166516-67-2 phenyl 2-azido-2-deoxy-1-thio-β-D-glucopyranoside 
• 236115-65-4 2-azido-2-deoxy-3,4,6-tri-O-benzyl-1-phenylthio-β-D-glucopyranoside 
• 236115-61-0 [(1S,2S,3R,4S,6R)-2-acetoxy-4,6-diazido-3-hydroxy-cyclohexyl] acetate 
• 236115-74-5 4-O-(2-azido-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-2-deoxystreptamine 
• 935871-52-6 2'-N-acetyl-paromamine 

Downstream Products

• 88897-23-8 1,3,2'-tri-N-p-tolylsulfonylparomamine 
• 289505-10-8 (2R,3S,4R,5R,6S)-5-azido-6-(((1R,2R,3S,4R,6S)-4, 6-diazido-2,3-dihydroxycyclohexyl)oxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol 
• 918800-23-4 (1S,2R,3R,4S,6R)-4,6-Diamino-3-((2S,3R,4S,5S,6R)-3,4-diamino-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-diol 
• 918800-42-7 (1S,2R,3R,4S,6R)-4,6-Diazido-3-((2S,3R,4S,5S,6R)-3,4-diazido-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-diol 
• 918800-29-0 Benzoic acid (2S,3R,4R,5S,6R)-3-azido-2-((1R,2R,3S,4R,6S)-4,6-diazido-2,3-dihydroxy-cyclohexyloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester 
• 918800-21-2 (2R,3R,4S,5R)-2-[(2S,3R,4R,5S,6R)-3-Amino-2-((1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxy-cyclohexyloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-5-hydroxymethyl-tetrahydro-furan-3,4-diol 
• 918800-19-8 NB₃₀ 
• 918800-20-1 (2R,3S,4R,5R,6S)-5-Amino-6-[(1R,2S,3S,4R,6S)-4,6-diamino-3-((2S,3R,4S,5R)-5-aminomethyl-3,4-dihydroxy-tetrahydro-furan-2-yloxy)-2-hydroxy-cyclohexyloxy]-2-hydroxymethyl-tetrahydro-pyran-3,4-diol 
• 918800-22-3 (2S,3R,4S,5R)-2-[(2S,3R,4R,5S,6R)-3-Amino-2-((1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxy-cyclohexyloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-5-aminomethyl-tetrahydro-furan-3,4-diol 
• 918800-26-7 Benzoic acid (2R,4aR,6S,7R,8R,8aS)-7-azido-6-((1R,2R,3S,4R,6S)-4,6-diazido-2,3-dihydroxy-cyclohexyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 918800-39-2 (2R,3R,4S,5R)-2-[(2S,3R,4R,5S,6R)-3-Azido-2-((1R,2R,3S,4R,6S)-4,6-diazido-2,3-dihydroxy-cyclohexyloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-5-hydroxymethyl-tetrahydro-furan-3,4-diol 
• 918800-38-1 (2S,3R,4S,5R)-2-[(2S,3R,4R,5S,6R)-3-Azido-2-((1R,2R,3S,4R,6S)-4,6-diazido-2,3-dihydroxy-cyclohexyloxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-5-azidomethyl-tetrahydro-furan-3,4-diol 
• 918800-30-3 C₂₄H₃₄N₁₂O₆ 
• 918800-40-5 (2R,3S,4R,5R,6S)-5-Azido-6-[(1R,2S,3S,4R,6S)-4,6-diazido-3-((2S,3R,4S,5R)-5-azidomethyl-3,4-dihydroxy-tetrahydro-furan-2-yloxy)-2-hydroxy-cyclohexyloxy]-2-hydroxymethyl-tetrahydro-pyran-3,4-diol 

Relevant articles and documents

Towards Catalytic Antibiotics: Redesign of Aminoglycosides To Catalytically Disable Bacterial Ribosomes

The emergence of multidrug-resistant pathogens that are resistant to the majority of currently available antibiotics is a significant clinical problem. The development of new antibacterial agents and novel approaches is therefore extremely important. We set out to explore the potential of catalytic antibiotics as a new paradigm in antibiotics research. Herein, we describe our pilot study on the design, synthesis, and biological testing of a series of new derivatives of the natural aminoglycoside antibiotic neomycin B for their potential action as catalytic antibiotics. The new derivatives showed significant antibacterial activity against wild-type bacteria and were especially potent against resistant and pathogenic strains including Pseudomonas aeruginosa and methicillin-resistant Staphylococcus aureus. Selected compounds displayed RNase activity even though the activity was not as high and specific as we would have expected. On the basis of the observed chemical and biochemical data, along with the comparative molecular dynamics simulations of the prokaryotic rRNA decoding site, we postulate that the rational design of catalytic antibiotics should involve not only their structure but also a comprehensive analysis of the rRNA A-site dynamics.

The neomycin biosynthetic gene cluster of Streptomyces fradiae NCIMB 8233: Genetic and biochemical evidence for the roles of two glycosyltransferases and a deacetylase

An efficient protocol has been developed for the genetic manipulation of Streptomyces fradiae NCIMB 8233, which produces the 2-deoxystreptamine (2-DOS)-containing aminoglycoside antibiotic neomycin. This has allowed the in vivo analysis of the respective roles of the glycosyltransferases Neo8 and Neo15, and of the deacetylase Neo16 in neomycin biosynthesis. Specific deletion of each of the neo8, neo15 and neo16 genes confirmed that they are all essential for neomycin biosynthesis. The pattern of metabolites produced by feeding putative pathway intermediates to these mutants provided unambiguous support for a scheme in which Neo8 and Neo15, whose three-dimensional structures are predicted to be highly similar, have distinct roles: Neo8 catalyses transfer of N-acetylglucosamine to 2-DOS early in the pathway, while Neo15 catalyses transfer of the same aminosugar to ribostamycin later in the pathway. The in vitro substrate specificity of Neo15, purified from recombinant Escherichia coli, was fully consistent with these findings. The in vitro activity of Neo16, the only deacetylase so far recognised in the neo gene cluster, showed that it is capable of acting in tandem with both Neo8 and Neo15 as previously proposed. However, the deacetylation of N-acetylglucosaminylribostamycin was still observed in a strain deleted of the neo16 gene and fed with suitable pathway precursors, providing evidence for the existence of a second enzyme in S. fradiae with this activity.

Efficient synthesis of neomycin B related aminoglycosides

Aminoglycosides 6'-hydroxyl-ribostamycin and 5-(α-neobiosamine)-2- deoxystreptamine were chemically synthesized. These compounds will be used as standards to compare RNA binding affinity and specificity with neomycin B. (C) 2000 Elsevier Science Ltd.