Names | |
---|---|
IUPAC name
(1S,7a'S,11a'R)-5',6',7a',10',11a'-Pentahydroxy-3'-methoxy-2,6,6-trimethyl-7',8',12'-trioxo-7',7a',8',11',11a',12'-hexahydro-1'H-spiro[cyclohex-2-ene-1,2'-cyclopenta[de]tetracene]-9'-carboxamide
| |
Identifiers | |
3D model (
JSmol)
|
|
ChemSpider | |
| |
| |
Properties | |
C30H29NO10 | |
Molar mass | 563.559 g·mol−1 |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Viridicatumtoxin B is a fungus-derived tetracycline-like antibiotic discovered in 2008. It was isolated from small amounts of penicillium fungi. A synthetic structure matching that of natural viridicatumtoxin B makes possible synthetic variants that match or surpass its antibiotic potency. [1]
Analogs lacking a hydroxyl group were even more effective than the original against Gram-positive bacteria. [1]
Concerns about solubility, biodegradation, availability and other issues must be resolved before clinical development begins. [1]
The substance was first isolated from the mycelium of liquid fermentation cultures of Penicillium species FR11. [2]
Based on mass spectrometry and nuclear magnetic resonance data, the substance was originally thought to be the 11a',12'- epoxide, [2] but the structure was later revised. [3]
Viridicatumtoxin B inhibited the growth of Staphylococcus aureus, including methicillin resistant S. aureus and quinolone-resistant S. aureus with a minimum inhibitory concentration of 0.5 μg/ml. That effect is similar to that of vancomycin, but 8 to 64 times greater than that of tetracycline. [2]
A complete total synthesis of viridicatumtoxin B, in racemic form, was completed in 2013 by the group of K. C. Nicolaou. [3] [4]
Names | |
---|---|
IUPAC name
(1S,7a'S,11a'R)-5',6',7a',10',11a'-Pentahydroxy-3'-methoxy-2,6,6-trimethyl-7',8',12'-trioxo-7',7a',8',11',11a',12'-hexahydro-1'H-spiro[cyclohex-2-ene-1,2'-cyclopenta[de]tetracene]-9'-carboxamide
| |
Identifiers | |
3D model (
JSmol)
|
|
ChemSpider | |
| |
| |
Properties | |
C30H29NO10 | |
Molar mass | 563.559 g·mol−1 |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Viridicatumtoxin B is a fungus-derived tetracycline-like antibiotic discovered in 2008. It was isolated from small amounts of penicillium fungi. A synthetic structure matching that of natural viridicatumtoxin B makes possible synthetic variants that match or surpass its antibiotic potency. [1]
Analogs lacking a hydroxyl group were even more effective than the original against Gram-positive bacteria. [1]
Concerns about solubility, biodegradation, availability and other issues must be resolved before clinical development begins. [1]
The substance was first isolated from the mycelium of liquid fermentation cultures of Penicillium species FR11. [2]
Based on mass spectrometry and nuclear magnetic resonance data, the substance was originally thought to be the 11a',12'- epoxide, [2] but the structure was later revised. [3]
Viridicatumtoxin B inhibited the growth of Staphylococcus aureus, including methicillin resistant S. aureus and quinolone-resistant S. aureus with a minimum inhibitory concentration of 0.5 μg/ml. That effect is similar to that of vancomycin, but 8 to 64 times greater than that of tetracycline. [2]
A complete total synthesis of viridicatumtoxin B, in racemic form, was completed in 2013 by the group of K. C. Nicolaou. [3] [4]