36889-15-3

Basic information

• Product Name: GENTAMICIN B
• Synonyms: d-streptamine,o-6-amino-6-deoxy-alpha-d-glucopyranosyl-(1-4)-o-(3-deoxy-4-c-me;gentamycinb;sch14342;thyl-3-(methylamino)-beta-l-arabinopyranosyl-(1-6))-2-deoxy-;2-(AMINOMETHYL)-6-[4,6-DIAMINO-3-(3,5-DIHYDROXY-5-METHYL-4-METHYLAMINO-OXAN-2-YL)OXY-2-HYDROXY-CYCLOHEXOXY]-OXANE-3,4,5-TRIOL;GENTAMICIN B;Betamicin;4-O-(6-Amino-6-deoxy-α-D-glucopyranosyl)-6-O-(3-deoxy-4-methyl-3-methylamino-β-L-arabinopyranosyl)-2-deoxy-D-streptamine
• CAS NO: 36889-15-3
• Molecular Formula: C₁₉H₃₈N₄O₁₀
• Molecular Weight: 482.53
• Mol File: 36889-15-3.mol

Chemical Properties

• Boiling Point: 751.2°Cat760mmHg
• Flash Point: 408.1°C
• Appearance: /
• Density: 1.5g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.634
• CAS DataBase Reference: GENTAMICIN B(CAS DataBase Reference)
• NIST Chemistry Reference: GENTAMICIN B(36889-15-3)
• EPA Substance Registry System: GENTAMICIN B(36889-15-3)

Safety Data

• Hazardous Substances Data: 36889-15-3(Hazardous Substances Data)

Usage

Uses

Used in Medical Industry:
GENTAMICIN B is used as an antibiotic for treating various types of infections, including respiratory and urinary tract infections, as well as infections in the blood, bone, and soft tissues. Its potent antibacterial properties make it an effective treatment option for a wide range of bacterial infections, helping to combat the spread of antibiotic-resistant strains and promote overall public health.

InChI:InChI=1/C19H38N4O10/c1-19(29)5-30-17(13(28)16(19)23-2)32-14-6(21)3-7(22)15(12(14)27)33-18-11(26)10(25)9(24)8(4-20)31-18/h6-18,23-29H,3-5,20-22H2,1-2H3/t6-,7+,8-,9-,10+,11-,12-,13-,14+,15-,16-,17-,18-,19+/m1/s1

Upstream product

• 1086092-62-7 C₁₅H₁₉NO₄S 
• 1086092-45-6 C₂₄H₂₆Cl₃NO₆S 
• 73362-91-1 (2S)-3,6'-bis-N-benzyloxycarbonyl-1-N-(2-benzyloxycarbonylamino-4-methylpentyloxycarbonyl)gentamicin B 

Downstream Products

• 66567-23-5 3,6'-bis-N-benzyloxycarbonylgentamicin B 

Relevant articles and documents

Reaction Catalyzed by GenK, a Cobalamin-Dependent Radical S-Adenosyl- l -methionine Methyltransferase in the Biosynthetic Pathway of Gentamicin, Proceeds with Retention of Configuration

Many cobalamin (Cbl)-dependent radical S-adenosyl-l-methionine (SAM) methyltransferases have been identified through sequence alignment and/or genetic analysis; however, few have been studied in vitro. GenK is one such enzyme that catalyzes methylation of the 6′-carbon of gentamicin X2 (GenX2) to produce G418 during the biosynthesis of gentamicins. Reported herein, several alternative substrates and fluorinated substrate analogs were prepared to investigate the mechanism of methyl transfer from Cbl to the substrate as well as the substrate specificity of GenK. Experiments with deuterated substrates are also shown here to demonstrate that the 6′-pro-R-hydrogen atom of GenX2 is stereoselectively abstracted by the 5′-dAdo· radical and that methylation occurs with retention of configuration at C6′. Based on these observations, a model of GenK catalysis is proposed wherein free rotation of the radical-bearing carbon is prevented and the radical SAM machinery sits adjacent rather than opposite to the Me-Cbl cofactor with respect to the substrate in the enzyme active site.

Semisynthetic Aminoglycoside Antibacterials. Part 10. Synthesis of Novel 1-N-Aminoalkoxycarbonyl and 1-N-Aminoalkylcarboxamido Derivatives of Sisomicin, Gentamicin B, Gentamicin C1a, and Kanamycin A

Suitably protected derivatives of sisomicin, 5-epi-sisomicin, gentamicin B, gentamicin C1a, and kanamycin A have been converted into a series of 1-N-alkoxycarbonyl, 1-N-aminoalkoxycarbonyl, 1-N-carboxamido, 1-N-alkylcarboxamido, and 1-N-aminoal

1-Desamino-1-hydroxy and 1-desamino-1-epi-hydroxy-4,6-di-o-(aminoglycosyl)-1,3-diaminocyclitols; 1-desamino-1-oxo-4,6-di-o-(aminoglycosyl)-1,3-diaminocyclitols, intermediates and use as antibacterial agents

This invention relates to the preparation of novel 1-desamino-1-oxo-aminoglycosides and their use as intermediates in the preparation of novel 1-desamino-1-hydroxy and 1-desamino-1-epi-hydroxyaminoglycoside antibacterial agents.

Garamine and derivatives thereof

This disclosure relates to the preparation of garamine, its use as an antibacterial, and its use as an intermediate in the novel processes for preparing novel pseudotrisaccharides containing a garamine moiety, and to the use of the novel pseudotrisaccharides as antimicrobial, anthelmintic, antiprotozoal and antiviral agents.