Spinosyn D 17-pseudoaglycone
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| Category | Others |
| Catalog number | BBF-04290 |
| CAS | 131929-55-0 |
| Molecular Weight | 604.77 |
| Molecular Formula | C34H52O9 |
| Purity | >95% by HPLC |
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Description
It is an acid degradation product produced by selective hydrolysis of the more labile forosamine saccharide in the 17-position in spinosyn D. It has only weak activity as an insecticide as the forosamine moiety is considered essential for potent activity.
Specification
| Synonyms | A 83543D pseudoaglycone; (2S,3aR,5aS,5bS,9S,13S,14R,16aS,16bS)-2-[(6-deoxy-2,3,4-tri-O-methyl-α-L-mannopyranosyl)oxy]-9-ethyl-2,3,3a,5a,5b,6,9,10,11,12,13,14,16a,16b-tetradecahydro-13-hydroxy-4,14-dimethyl-1H-as-indaceno[3,2-d]oxacyclododecin-7,15-dione |
| Storage | Store at -20°C |
| IUPAC Name | (1S,2S,5R,7S,9S,10S,14R,15S,19S)-19-ethyl-15-hydroxy-4,14-dimethyl-7-[(2R,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyloxan-2-yl]oxy-20-oxatetracyclo[10.10.0.02,10.05,9]docosa-3,11-diene-13,21-dione |
| Canonical SMILES | CCC1CCCC(C(C(=O)C2=CC3C4CC(CC4C(=CC3C2CC(=O)O1)C)OC5C(C(C(C(O5)C)OC)OC)OC)C)O |
| InChI | InChI=1S/C34H52O9/c1-8-20-10-9-11-28(35)18(3)30(37)27-15-25-23(26(27)16-29(36)42-20)12-17(2)22-13-21(14-24(22)25)43-34-33(40-7)32(39-6)31(38-5)19(4)41-34/h12,15,18-26,28,31-35H,8-11,13-14,16H2,1-7H3/t18-,19+,20+,21-,22+,23-,24-,25-,26+,28+,31+,32-,33-,34+/m1/s1 |
| InChI Key | PGGPPEHRBUYMQU-QEGHUGIASA-N |
| Source | Semi-synthetic |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | Parasites |
| Boiling Point | 735.1±60.0°C at 760 mmHg |
| Density | 1.2±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1. Conversion of spinosyn A and spinosyn D to their respective 9- and 17-pseudoaglycones and their aglycones
J W Paschal, H A Kirst, L C Creemer J Antibiot (Tokyo) . 1998 Aug;51(8):795-800. doi: 10.7164/antibiotics.51.795.
Forosamine at the 17-position of spinosyns A and D was hydrolyzed under mild acidic conditions to give the corresponding 17-pseudoaglycones. The tri-O-methylrhamnose at the 9-position of the 17-pseudoaglycone of spinosyn A was hydrolyzed under more vigorous acidic conditions to give the aglycone of spinosyn A. However, these conditions led to decomposition of the 17-pseudoaglycone of spinosyn D, presumably due to more facile protonation of the 5,6-double bond to produce a tertiary carbonium ion which undergoes further rearrangements. Spinosyns J and L (3'-O-demethyl spinosyn A and D, respectively) obtained from fermentation of biosynthetically-blocked mutant strains of Saccharopolyspora spinosa, were oxidized to give the corresponding 3'-keto-derivatives and the resultant keto-sugars were then beta-eliminated under basic conditions to give the 9-pseudoaglycones of spinosyns A and D respectively. Forosamine at the 17-position of the 9-pseudoaglycone of spinosyn D was then readily hydrolyzed to yield the aglycone of spinosyn D.
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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 ╳
