Venturicidin B
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| Category | Antibiotics |
| Catalog number | BBF-03440 |
| CAS | 33538-72-6 |
| Molecular Weight | 706.94 |
| Molecular Formula | C40H66O10 |
| Purity | >95% by HPLC |
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Description
The macrolide antibiotic isolated from a streptomyces sp. It is a potent inhibitor of mitochondrial ATP synthase complex acting on the F0 membrane sector. It is originally isolated as an antifungal agent.
Specification
| Synonyms | Aabomycin A2; (1R,2E,7R,8E,10R,12R,13S,17R)-7-[(2R,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-17-hydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4,6-dimethyl-7-oxononan-2-yl]-2,10,12,20-tetramethyl-14,21-dioxabicyclo[15.3.1]henicosa-2,8,19-trien-15-one |
| Storage | Store at-20°C |
| IUPAC Name | (1R,5S,6R,8R,9E,11R,15E,17R)-11-[(2R,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-1-hydroxy-5-[(2R,4R,5S,6S)-5-hydroxy-4,6-dimethyl-7-oxononan-2-yl]-6,8,16,18-tetramethyl-4,21-dioxabicyclo[15.3.1]henicosa-9,15,18-trien-3-one |
| Canonical SMILES | CCC(=O)C(C)C(C(C)CC(C)C1C(CC(C=CC(CCCC=C(C2C(=CCC(O2)(CC(=O)O1)O)C)C)OC3CC(C(C(O3)C)O)O)C)C)O |
| InChI | InChI=1S/C40H66O10/c1-10-32(41)29(8)36(44)26(5)20-28(7)38-27(6)19-23(2)15-16-31(48-35-21-33(42)37(45)30(9)47-35)14-12-11-13-24(3)39-25(4)17-18-40(46,50-39)22-34(43)49-38/h13,15-17,23,26-31,33,35-39,42,44-46H,10-12,14,18-22H2,1-9H3/b16-15+,24-13+/t23-,26+,27+,28+,29+,30+,31+,33+,35-,36-,37+,38-,39+,40+/m0/s1 |
| InChI Key | VIOYQVOQUWWSAB-KEXSXYLYSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | White Lyophilisate |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 823.4°C at 760 mmHg |
| Melting Point | 145-149°C |
| Density | 1.1 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Poor water solubility. |
Reference Reading
1. [The use of microbial and enzymatic function in organic synthesis. Total synthesis of the aglycone of venturicidins A and B]
H Akita Yakugaku Zasshi . 1990 Nov;110(11):789-806. doi: 10.1248/yakushi1947.110.11_789.
The synthesis of chiral synthons by means of microbial and enzymatic function and its application to the synthesis of complex, bioactive substances, the aglycone of venturicidins A and B are reviewed. 1) The syntheses of chiral synthons having two chiral centers are described based on the microbial asymmetric reduction of alpha-methyl beta-keto esters or enzymatic asymmetric hydrolysis of alpha-methyl beta-acetoxy esters. 2) The new chiral synthons synthesized in 1) have been successfully applied for the total syntheses of oudemansins A and B. 3) Purification and properties of the asymmetric reduction enzyme of alpha-methyl beta-keto esters in Saccharomyces cerevisiae or Saccharomyces fermentati were investigated. 4) Formal total synthesis of (-)-indolmycin is described based on the asymmetric hydrolysis of alpha-acetoxy ester with lipases. 5) Enzymatic hydrolysis in organic solvents for kinetic resolution of water-insoluble alpha-acyloxy esters with immobilized lipases is described. 6) The first total synthesis of the aglycone of venturicidins A and B has been successfully achieved from the new chiral synthon based on the developed method in 1).
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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 ╳
