Viridicatin
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| Category | Antibiotics |
| Catalog number | BBF-02968 |
| CAS | 129-24-8 |
| Molecular Weight | 237.25 |
| Molecular Formula | C15H11NO2 |
| Purity | >99% by HPLC |
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Description
It is a quinoline aromatic antibiotic produced by the strain of Pen. viridicatum, Pen. cyclopium SM-72 and Pen. puberulum. It has anti-gram-positive bacteria and mycobacteria effects.
Specification
| Synonyms | 2,3-dihydroxy-4-phenylquinoline; 2(1H)-Quinolinone, 3-hydroxy-4-phenyl- |
| Storage | Store at -20°C |
| IUPAC Name | 3-hydroxy-4-phenyl-1H-quinolin-2-one |
| Canonical SMILES | C1=CC=C(C=C1)C2=C(C(=O)NC3=CC=CC=C32)O |
| InChI | InChI=1S/C15H11NO2/c17-14-13(10-6-2-1-3-7-10)11-8-4-5-9-12(11)16-15(14)18/h1-9,17H,(H,16,18) |
| InChI Key | QSRVMXWVVMILDI-UHFFFAOYSA-N |
| Source | Penicillium sp. |
Properties
| Appearance | Colorless Acicular Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Mycobacteria |
| Boiling Point | 476.7±45.0°C at 760 mmHg |
| Melting Point | 268-269°C |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, DMF, DMSO |
Reference Reading
1. Enzymatic one-step ring contraction for quinolone biosynthesis
Hiroshi Hashimoto, Yi Tang, Pier Alexandre Champagne, Kodai Hara, Shinji Kishimoto, Yuichiro Hirayama, Kendall N Houk, Kenji Watanabe Nat Commun . 2018 Jul 19;9(1):2826. doi: 10.1038/s41467-018-05221-5.
The 6,6-quinolone scaffolds on which viridicatin-type fungal alkaloids are built are frequently found in metabolites that display useful biological activities. Here we report in vitro and computational analyses leading to the discovery of a hemocyanin-like protein AsqI from the Aspergillus nidulans aspoquinolone biosynthetic pathway that forms viridicatins via a conversion of the cyclopenin-type 6,7-bicyclic system into the viridicatin-type 6,6-bicyclic core through elimination of carbon dioxide and methylamine through methyl isocyanate.
2. Non-heme dioxygenase catalyzes atypical oxidations of 6,7-bicyclic systems to form the 6,6-quinolone core of viridicatin-type fungal alkaloids
Kinya Hotta, Clay C C Wang, Kenji Watanabe, Hiroshi Noguchi, Fumi Koyama, Hidenori Tanaka, Noriyasu Ishikawa Angew Chem Int Ed Engl . 2014 Nov 17;53(47):12880-4. doi: 10.1002/anie.201407920.
The 6,6-quinolone scaffold of the viridicatin-type of fungal alkaloids are found in various quinolone alkaloids which often exhibit useful biological activities. Thus, it is of interest to identify viridicatin-forming enzymes and understand how such alkaloids are biosynthesized. Here an Aspergillal gene cluster responsible for the biosynthesis of 4'-methoxyviridicatin was identified. Detailed in vitro studies led to the discovery of the dioxygenase AsqJ which performs two distinct oxidations: first desaturation to form a double bond and then monooxygenation of the double bond to install an epoxide. Interestingly, the epoxidation promotes non-enzymatic rearrangement of the 6,7-bicyclic core of 4'-methoxycyclopenin into the 6,6-quinolone viridicatin scaffold to yield 4'-methoxyviridicatin. The finding provides new insight into the biosynthesis of the viridicatin scaffold and suggests dioxygenase as a potential tool for 6,6-quinolone synthesis by epoxidation of benzodiazepinediones.
3. Regioselective Ring Expansion of Isatins with In Situ Generated α-Aryldiazomethanes: Direct Access to Viridicatin Alkaloids
Bathini Nagendra Babu, Kesari Lakshmi Manasa, Yellaiah Tangella, Namballa Hari Krishna, B Sridhar, Ahmed Kamal Org Lett . 2018 Jun 15;20(12):3639-3642. doi: 10.1021/acs.orglett.8b01417.
A novel efficient one-pot regioselective ring-expansion reaction of isatins with in situ generated α-aryl/heteroaryldiazomethanes for the construction of viridicatin alkaloids has been described under metal-free conditions. The utility of this protocol is further demonstrated in the synthesis of naturally occurring viridicatin, viridicatol, and substituted 3- O-methyl viridicatin and their scale up.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
