(3'R,3aS,4S,4'S,5'R,6R,6'R,7S,7aS)-4-[(1R,2S,3R,5S,6R)-3-amino-2,6-dihydroxy-5-(methylamino)cyclohexyl]oxy-6'-(1-amino-2-hydroxyethyl)-6-(hydroxymethyl)spiro[4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2,2'-oxane]-3',4',5',7-tetrol

Base Information

• Chemical Name: (3'R,3aS,4S,4'S,5'R,6R,6'R,7S,7aS)-4-[(1R,2S,3R,5S,6R)-3-amino-2,6-dihydroxy-5-(methylamino)cyclohexyl]oxy-6'-(1-amino-2-hydroxyethyl)-6-(hydroxymethyl)spiro[4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2,2'-oxane]-3',4',5',7-tetrol
• CAS No.: 31282-04-9
• Molecular Formula: C₂₀H₃₇N₃O₁₃
• Molecular Weight: 527.526
• Hs Code.: 29419059
• European Community (EC) Number: 250-545-5
• UN Number: 3462
• ChEMBL ID: CHEMBL326396
• Metabolomics Workbench ID: 50724
• Wikipedia: Hygromycin_B
• Mol file: 31282-04-9.mol

Synonyms:Hygromycin B

Chemical Property of (3'R,3aS,4S,4'S,5'R,6R,6'R,7S,7aS)-4-[(1R,2S,3R,5S,6R)-3-amino-2,6-dihydroxy-5-(methylamino)cyclohexyl]oxy-6'-(1-amino-2-hydroxyethyl)-6-(hydroxymethyl)spiro[4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2,2'-oxane]-3',4',5',7-tetrol

Chemical Property:

• Appearance/Colour: Amorphous solid or tan powder.
• Melting Point: 160-180 °C
• Refractive Index: 1.672
• Boiling Point: 897.6 °C at 760 mmHg
• PKA: 7.1, 8.8(at 25℃)
• Flash Point: 496.7 °C
• PSA: 272.06000
• Density: 1.67 g/cm³
• LogP: -5.47910
• Storage Temp.: 2-8°C
• Solubility.: H2O: 50 mg/mL As a stock solution. Stock solutions should b
• Water Solubility.: Miscible with water, methanol, buffer solution and ethanol. Immiscible with less polar solvents.
• XLogP3: -6.6
• Hydrogen Bond Donor Count: 11
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 6
• Exact Mass: 527.23263824
• Heavy Atom Count: 36
• Complexity: 756
• Transport DOT Label: Poison

Purity/Quality:

97%HPLC ^*data from raw suppliers

Hygromycin B, Streptomyces hygroscopicus ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+, Xn
• Hazard Codes: T+,Xn,T
• Statements: 26/27/28-41-42/43-40-36-23/24/25
• Safety Statements: 23-26-28-36/37/39-45-22-36-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CNC1CC(C(C(C1O)OC2C3C(C(C(O2)CO)O)OC4(O3)C(C(C(C(O4)C(CO)N)O)O)O)O)N
• Isomeric SMILES: CN[C@H]1C[C@H]([C@@H]([C@H]([C@@H]1O)O[C@H]2[C@@H]3[C@H]([C@H]([C@H](O2)CO)O)OC4(O3)[C@@H]([C@H]([C@H]([C@H](O4)C(CO)N)O)O)O)O)N
• Description: Hygromycin B is an aminoglycoside antibiotic that has been found in S. hygroscopicus. It is active against E. coli (MIC = 150 μg/ml) and cytotoxic to both prokaryotic and eukaryotic cells via inhibition of protein synthesis. Hygromycin B has commonly been used in molecular and cell biology applications to select for transformed cells expressing the E. coli hygromycin resistance genes hyg or hph.
• Uses: antibacterial, anthelmintic; LD50 ip (rat) 63mg/Kg Hygromycin B, a selective antibiotic that is effective on most bacteria, fungi and higher eukaryotes, inhibits protein synthesis by interfering with translocation and causing mistranslation at the 70S ribosome Hygromycin B is an aminoglycoside and a selective antibiotic agent for the hph gene. Hygromycin B inhibits protein synthesis by interfering with translocation and causing mistranslation at the 70S rib osome Hygromycin B is a trisaccharide aminoglycoside with a terminal cyclitol produced by Streptomyces hygroscopicus, reported by researchers at Eli Lily in the early 1950s. Hygromycin B belongs to the destomycin family of aminoglycosides which contain a unique cyclic structure linking the terminal saccharide. Hygromycin B exhibits broad spectrum antibiotic and anthelmintic activity, and is used as a feed additive for swine and poultry. Hygromycin B inhibits polypeptide synthesis by binding peptidyl-tRNA and preventing translocation by Elongation Factor 2.

Refernces

SYNTHESIS OF DESTOMIC AND epi-DESTOMIC ACID, AND THEIR C-6 EPIMERS

10.1016/S0008-6215(00)82223-5

The research focuses on the synthesis of four stereoisomers of 6-amino-6-deoxyheptonic acid, specifically destomic acid (1), epi-destomic acid (3), and their C-6 epimers (2 and 4), which are components of a new type of aminocyclitol antibiotic: destomycins. The purpose of this research was to develop a method for the synthesis of these acids not only for structural confirmation but also for the chemical synthesis of destomycin-group antibiotics. The synthesis involved the use of D-glycero-D-galacto (1 and 2) and L-glycero-D-gulo (3 and 4) configurations, derived from D-glycero- (8) and D-galacto-dialdose (23) derivatives, respectively. The researchers successfully synthesized the target compounds and confirmed their structures by comparing their physical data and chromatographic behavior with those of naturally occurring destomic and epi-destomic acids. The study concluded that the synthetic destomic acid (1) and epi-destomic acid (3) were identical to the naturally occurring ones, thereby achieving the goal of synthesizing these complex organic compounds.