Avermectin B1a monosaccharide
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04209 |
| CAS | 71831-09-9 |
| Molecular Weight | 728.91 |
| Molecular Formula | C41H60O11 |
| Purity | >95% by HPLC |
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Description
It is an acid degradation product produced by selective hydrolysis of the terminal saccharide unit of avermectin. It is a potent inhibitor of nematode larval development. It has no paralytic activity.
Specification
| Synonyms | 4'-O-de(2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranosyl)-5-O-demethyl-avermectin A1a; 5-O-Demethyl-4'-O-de(2,6-dideoxy-3-O-methyl-α-L-glucopyranosyl)avermectin A1a; MSB 1a |
| Storage | Store at -20°C |
| IUPAC Name | (1'R,2R,3S,4'S,6S,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-2-[(2S)-butan-2-yl]-21',24'-dihydroxy-12'-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-3,11',13',22'-tetramethylspiro[2,3-dihydropyran-6,6'-3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene]-2'-one |
| Canonical SMILES | CCC(C)C1C(C=CC2(O1)CC3CC(O2)CC=C(C(C(C=CC=C4COC5C4(C(C=C(C5O)C)C(=O)O3)O)C)OC6CC(C(C(O6)C)O)OC)C)C |
| InChI | InChI=1S/C41H60O11/c1-9-22(2)37-25(5)15-16-40(52-37)20-30-18-29(51-40)14-13-24(4)36(50-33-19-32(46-8)35(43)27(7)48-33)23(3)11-10-12-28-21-47-38-34(42)26(6)17-31(39(44)49-30)41(28,38)45/h10-13,15-17,22-23,25,27,29-38,42-43,45H,9,14,18-21H2,1-8H3/b11-10+,24-13+,28-12+/t22-,23-,25-,27-,29+,30-,31-,32-,33-,34+,35-,36-,37+,38+,40+,41+/m0/s1 |
| InChI Key | ZBVWYDMYMRLKIV-OESCZRLOSA-N |
| Source | Semi-synthetic |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | Parasites |
| Boiling Point | 861.8±65.0°C at 760 mmHg |
| Density | 1.2±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1. The metabolism of avermectins B1a, H2B1a, and H2B1b by liver microsomes
A Y Lu, W J VandenHeuvel, R W Walker, A Rosegay, R Taub, T A Jacob, M A Walsh, B Arison, R Buhs, S Avermitilis, J S Walsh, G T Miwa, E Sestokas Drug Metab Dispos . 1982 May-Jun;10(3):268-74.
The avermectins area a new class of structurally related antiparasitic agents isolated from Streptomyces avermitilis. The major polar metabolites isolated from in vitro incubations of [3H]avermectins B1a, H2B1a, and H2B1b with either rat or steer liver microsomes have been isolated and identified as the C24-methyl alcohols of the parent compounds. A smaller quantity of a more polar metabolite has also been identified as the monosaccharide of the C24-methyl alcohols of avermectin H2H1b from rat liver microsomal incubation and avermectin H2B1a from steer liver microsomal incubation. The mass spectra and 300-MHz 1H-NMR spectra permitted assignment of structures to these metabolites. Together these two metabolites represent 50-80% of the total radioactivity more polar than the parent compounds. The metabolite profiles on reverse-phase HPLC demonstrate that the rat and steer are qualitatively similar in the production of these two polar metabolites.
2. Studies on the biosynthesis of avermectins
T S Chen, E S Inamine Arch Biochem Biophys . 1989 May 1;270(2):521-5. doi: 10.1016/0003-9861(89)90534-1.
To elucidate the pathway of avermectin biosynthesis, the biosynthetic relationships of avermectins A1a, A2a, B1a, B2a, and their respective monosaccharides and aglycones were studied. 14C-labeled avermectin compounds prepared from [1-14C]acetate were fed to Streptomyces avermitilis strain MA5502 and their metabolites were determined. Two furan ring-free aglycones, 6,8a-seco-6,8a-deoxy-5-keto avermectin B1a and B2a, have been isolated from the fermentation broth of a blocked mutant of S. avermitilis. Addition of the compounds and a semisynthetic compound, 5-keto avermectin B2a aglycone, to the fermentation medium of a second blocked mutant established that the two compounds are intermediates in the avermectin biosynthetic pathway immediately preceding avermectin aglycones.
3. The effect of inorganic phosphate on the production of avermectin in Streptomyces avermitilis
E Curdová, J Zima, Z Vanĕk, V Jechová J Basic Microbiol . 1989;29(6):341-6. doi: 10.1002/jobm.3620290607.
The effect of phosphate on the production of avermectin B1a, growth and utilization of glucose in the course of cultivation of Streptomyces avermitilis on a complex and chemically defined medium has been studied. Phosphate added at the beginning of cultivation at 1-20 mmol/l did not distinctly affect the production of secondary metabolite. From the results it follows that the biosynthesis of avermectin tolerates high concentrations of phosphate in the medium.
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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 ╳
