Spinosyn D aglycone
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| Category | Others |
| Catalog number | BBF-04292 |
| CAS | 149439-79-2 |
| Molecular Weight | 416.55 |
| Molecular Formula | C25H36O5 |
| Purity | >95% by HPLC |
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Description
It is an acid degradation product produced by hydrolysis of both saccharide groups on spinosyn D. It has only weak activity as an insecticide as the saccharides are considered essential for potent activity.
Specification
| Synonyms | A-83543D aglycone; (2S,3aR,5aS,5bS,9S,13S,14R,16aS,16bS)-9-ethyl-2,3,3a,5a,5b,6,9,10,11,12,13,14,16a,16b-tetradecahydro-2,13-dihydroxy-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-7,15-dihydroxy-4,14-dimethyl-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)O)C)O |
| InChI | InChI=1S/C25H36O5/c1-4-16-6-5-7-23(27)14(3)25(29)22-11-20-18(21(22)12-24(28)30-16)8-13(2)17-9-15(26)10-19(17)20/h8,11,14-21,23,26-27H,4-7,9-10,12H2,1-3H3/t14-,15-,16+,17+,18-,19-,20-,21+,23+/m1/s1 |
| InChI Key | XJXGESFEOGOUOJ-OSPFSVQDSA-N |
| Source | Semi-synthetic |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | Parasites |
| Boiling Point | 641.9±55.0°C (Predicted) |
| Density | 1.19±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1. Glycosylation engineering of spinosyn analogues containing an L-olivose moiety
Isabelle Carletti,Sabine Gaisser,Christine J Martin,Thomas C Sparks,Ursula Schell,Barrie Wilkinson,Paul R Graupner Org Biomol Chem . 2009 Apr 21;7(8):1705-8. doi: 10.1039/b900233b.
Biosynthetic genes encoding proteins involved in the first steps of deoxyhexose biosynthesis from D-glucose-1-phosphate were expressed in Saccharopolyspora erythraea. The resulting mutant was able to accumulate and utilise TDP-L-olivose. Co-expression of the spinosyn glycosyl transferase SpnP in the resulting mutant endowed upon it the ability to biotransform exogenously added spinosyn aglycones to yield novel spinosyn analogues.
2. Heterologous expression in Saccharopolyspora erythraea of a pentaketide synthase derived from the spinosyn polyketide synthase
Rose M Sheridan,James C Staunton,Steven G Kendrew,Peter F Leadlay,Christine J Martin,Barrie Wilkinson,Máire C Timoney Org Biomol Chem . 2003 Dec 7;1(23):4144-7. doi: 10.1039/b310740j.
A truncated version of the spinosyn polyketide synthase comprising the loading module and the first four extension modules fused to the erythromycin thioesterase domain was expressed in Saccharopolyspora erythraea. A novel pentaketide lactone product was isolated, identifying cryptic steps of spinosyn biosynthesis and indicating the potential of this approach for the biosynthetic engineering of spinosyn analogues. A pathway for the formation of the tetracyclic spinosyn aglycone is proposed.
3. Conversion of spinosyn A and spinosyn D to their respective 9- and 17-pseudoaglycones and their aglycones
H A Kirst,J W Paschal,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 ╳
