Spinosyn A aglycone
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Others |
| Catalog number | BBF-04291 |
| CAS | 149560-97-4 |
| Molecular Weight | 402.52 |
| Molecular Formula | C24H34O5 |
| Purity | >95% by HPLC |
Online Inquiry
Description
It is an acid degradation product produced by hydrolysis of both saccharide groups on spinosyn. It has only weak activity as an insecticide as the saccharides are considered essential for potent activity.
Specification
| Synonyms | (-)-spinosyn A aglycon; A 83543A Aglycon; (2R,3aS,5aR,5bS,9S,13S,14R,16aS,16bR)-9-ethyl-2,13-dihydroxy-14-methyl-2,3,3a,5a,5b,6,9,10,11,12,13,14,16a,16b-tetradecahydro-1H-as-indaceno[3,2-d][1]oxacyclododecine-7,15-dione |
| Storage | Store at -20°C |
| IUPAC Name | (1S,2R,5S,7R,9R,10S,14R,15S,19S)-19-ethyl-7,15-dihydroxy-14-methyl-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)O)C)O |
| InChI | InChI=1S/C24H34O5/c1-3-16-5-4-6-22(26)13(2)24(28)21-11-19-17(20(21)12-23(27)29-16)8-7-14-9-15(25)10-18(14)19/h7-8,11,13-20,22,25-26H,3-6,9-10,12H2,1-2H3/t13-,14-,15-,16+,17-,18-,19-,20+,22+/m1/s1 |
| InChI Key | DIHUILSVOGYVDG-MRAVEKNJSA-N |
| Source | Semi-synthetic |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | Parasites |
| Boiling Point | 637.8±55.0°C (Predicted) |
| Density | 1.20±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1. Total synthesis of (-)-spinosyn A: examination of structural features that govern the stereoselectivity of the key transannular Diels-Alder reaction
Dustin J Mergott, William R Roush, SusAnn M Winbush J Org Chem . 2008 Mar 7;73(5):1818-29. doi: 10.1021/jo7024515.
A study of elements of stereochemical control in transannular Diels-Alder reactions leading to the decahydro-as-indacene core of (-)-spinosyn A is described. Initial studies focused on macrocyclic pentaene 9, which includes C(6)-Br and C(8)-OTBS substituents. Excellent selectivity (>95:5) was observed in the cycloaddition of 9 as a consequence of 1,3-allylic strain interactions involving the C(6) and C(8) substituents in the disfavored TS-2. The major cycloadduct 22 was used in a formal synthesis of (-)-spinosyn A. The TDA cyclizations of 12 (which lacks the C(8)-OTBS unit of 9), 13 (which lacks the C(6)-Br substituent of 12), and 14 (which lacks the C(6)-Br and C(21)-Et substituents of 12) were also studied. Macrocycles 12 and 13 served as precursors to (-)-spinosyn A and the (-)-spinosyn A aglycon (34), respectively. It is striking that substrates 12-14 give very similar distributions of transannular Diels-Alder cycloadducts, indicating that the C(6)-Br and C(21)-stereocenter do not play a significant role in the diastereoselectivity of the TDA cycloaddition of spinosyn A precursor 12. It is likely that some as yet unidentified conformational or structural features of macrocycles 12-14 contribute to the levels of diastereoselectivity achieved, since these TDA reactions are more selective for the C(7)-C(9) stereochemical relationship found in the natural product than are the IMDA reactions of trienes 4 and 7.
2. Heterologous expression in Saccharopolyspora erythraea of a pentaketide synthase derived from the spinosyn polyketide synthase
Christine J Martin, Máire C Timoney, Peter F Leadlay, Steven G Kendrew, James C Staunton, Barrie Wilkinson, Rose M Sheridan 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. A semisynthesis of 3'- O-ethyl-5,6-dihydrospinosyn J based on the spinosyn A aglycone
Anjun Liu, Hongxin Chai, Shenglan Liu, Jiarong Li, Kai Zhang, Lamusi A Beilstein J Org Chem . 2017 Dec 6;13:2603-2609. doi: 10.3762/bjoc.13.257.
Spinetoram, a mixture of 3'-O-ethyl-5,6-dihydrospinosyn J (XDE-175-J, major component) and 3'-O-ethylspinosyn L (XDE-175-L, minor component), is a novel kind of green and efficient insecticide with a broad range of action against various insects. Nowadays, spinetoram is widely used in agriculture and food storage. This work reports a 7-step semisynthesis of 3'-O-ethyl-5,6-dihydrospinosyn J from spinosyn A aglycone. The C9-OH and C17-OH of the aglycone are successively connected to 3-O-ethyl-2,4-di-O-methylrhamnose and D-forosamine after selective protection and deprotection steps. Then, with 10% Pd/C as catalyst, the 5,6-double bond of the macrolide was selectively reduced to afford 3'-O-ethyl-5,6-dihydrospinosyn J. In addition, the 3-O-ethyl-2,4-di-O-methylrhamnose is synthesized from rhamnose which is available commercially, while the D-forosamine and aglycone are obtained via the hydrolysis of spinosyn A. High yields were obtained in each step, and all intermediates in the synthesis were characterized by1H NMR,13C NMR and MS techniques. This study can be helpful for developing an efficient chemical synthesis of spinetoram, and it also offers opportunities to synthesize spinosyn analogues and rhamnose derivatives.
Recommended Products
| BBF-01826 | Deoxymannojirimycin | Inquiry |
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
| BBF-03755 | Actinomycin D | Inquiry |
| BBF-03754 | Castanospermine | Inquiry |
| BBF-02614 | Nystatin | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
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 ╳
