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PyOxim

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

PyOxim is a novel reagent which mediates coupling reactions with efficiencies superior to HATU and PyBOP and comparable to COMU. It is has excellent solubility in DMF and is stable in solution under an inert atmosphere for two days. Unlike HATU and HBTU, it cannot cause chain terminating side reactions and is, therefore, ideal for the synthesis of cyclic peptides. Furthermore, it is not explosive under normal operating conditions and is less likely to exhibit allergenicity compared to other coupling reagents.

Category
Peptide Synthesis Reagents
Catalog number
BAT-006278
CAS number
153433-21-7
Molecular Formula
C17H29F6N5O3P2
Molecular Weight
527.38
IUPAC Name
[(E)-(1-cyano-2-ethoxy-2-oxoethylidene)amino]oxy-tripyrrolidin-1-ylphosphanium;hexafluorophosphate
Synonyms
pyoxime; AS-10531; SC-13336; CS-0068035; K-4853; J-009012; (Ethyl cyano(hydroxyimino)acetato)-tri-(1-pyrrolidinyl)-phosphonium hexafluorophosphate; [cyano-(ethoxycarbonyl)methyleneaminooxy]tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; (T-4)-[ethyl cyano(hydroxyimino)acetato-O2]tri-1-pyrrolidinyl-Phosphorus(1+) hexafluorophosphate(1-); (T-​4)​-[ethyl 2-​cyano-​2-​[(hydroxy-​κO)​imino]​acetato]​tri-​1-​pyrrolidinyl-Phosphorus(1+) hexafluorophosphate(​1-​)
Appearance
White Solid Powder
Purity
> 98% (HPLC)
Melting Point
165-175 °C
Storage
RT
Solubility
Soluble in Dichloromethane, Hexane; Slightly soluble in Chloroform, Methanol
InChI
InChI=1S/C17H29N5O3P.F6P/c1-2-24-17(23)16(15-18)19-25-26(20-9-3-4-10-20,21-11-5-6-12-21)22-13-7-8-14-22;1-7(2,3,4,5)6/h2-14H2,1H3;/q+1;-1/b19-16+;
InChI Key
RDWDVLFMPFUBDV-PXMDEAMVSA-N
Canonical SMILES
CCOC(=O)C(=NO[P+](N1CCCC1)(N2CCCC2)N3CCCC3)C#N.F[P-](F)(F)(F)(F)F
1. Trichoderma asperellum reduces phoxim residue in roots by promoting plant detoxification potential in Solanum lycopersicum L
Shuangchen Chen, Yaru Yan, Yaqi Wang, Meijuan Wu, Qi Mao, Yifei Chen, Jingjing Ren, Airong Liu, Xiaomin Lin, Golam Jalal Ahammed Environ Pollut. 2020 Apr;259:113893. doi: 10.1016/j.envpol.2019.113893. Epub 2019 Dec 30.
Phoxim, a broad-spectrum organophosphate pesticide, is widely used in agriculture to control insect pests in vegetable crops as well as in farm mammals. However, the indiscriminate use of phoxim has increased its release into the environment, leading to the contamination of plant-based foods such as vegetables. In this study, we investigated the effect of Trichoderma asperellum (TM, an opportunistic fungus) on phoxim residue in tomato roots and explored the mechanisms of phoxim metabolism through analysis of detoxification enzymes and gene expression. Degradation kinetics of phoxim showed that TM inoculation rapidly and significantly reduced phoxim residues in tomato roots. Phoxim concentrations at 5d, 10d and 15d post treatment were 75.12, 65.71 and 77.45% lower in TM + phoxim than only phoxim treatment, respectively. The TM inoculation significantly increased the glutathione (GSH) content, the activity of glutathione S-transferase (GST) and the transcript levels of GSH, GST1, GST2 and GST3 in phoxim-treated roots. In addition, the activity of peroxidase and polyphenol peroxidase involved in the xenobiotic conversion also increased in TM + phoxim treatment. The expression of detoxification genes, such as CYP724B2, GR, ABC2 and GPX increased by 3.82, 3.08, 7.89 and 2.46 fold, respectively in TM + phoxim compared with only phoxim. Similarly, the content of ascorbate (AsA) and the ratio of AsA to dehydroascorbate increased by 45.16% and 57.34%, respectively in TM + phoxim-treated roots. Our results suggest that TM stimulates plant detoxification potential in all three phases (conversion, conjugation and sequestration) of xenobiotc metabolism, leading to a reduced phoxim residue in tomato roots.
2. Evaluation of phoxim toxicity on aquatic and zebrafish intestinal microbiota by metagenomics and 16S rRNA gene sequencing analysis
Jinfeng Zhang, Qi Zhang, Zhenyan Zhang, Zhigao Zhou, Tao Lu, Liwei Sun, Haifeng Qian Environ Sci Pollut Res Int. 2022 Sep;29(42):63017-63027. doi: 10.1007/s11356-022-20325-8. Epub 2022 Apr 21.
Phoxim is one of the main organophosphorus pesticides used in agricultural production. However, little information is known about how it affects the aquatic microbial community and the intestinal microbiota of fish. Herein, we utilized shotgun metagenomics and 16S rRNA gene sequencing to reveal the aquatic eco-risk of phoxim. Seven days of phoxim exposure significantly changed the composition of aquatic microbial community, obliterated the interactions between microorganisms, and thus reduced the complexity and stability of the microbial community. During long-time exposure (i.e., 14 days), most of the ecological functions were restored due to the redundancy of the microbial community. However, phoxim exposure promoted the dissemination of elfamycin resistance gene. The zebrafish gut microbial community also recovered from a temporary ecological disorder of aquatic microbiota, but phoxim continually affected zebrafish growth and swimming behavior. Overall, our results demonstrated that phoxim exposure significantly changed the structure and function of the microbial community and displayed a negative impact on freshwater ecosystems in a short exposure time.
3. Effects of phoxim exposure on gut microbial composition in the silkworm, Bombyx mori
Fanchi Li, Mengxue Li, Tingting Mao, Hui Wang, Jian Chen, Zhengting Lu, Jianwei Qu, Yilong Fang, Zhiya Gu, Bing Li Ecotoxicol Environ Saf. 2020 Feb;189:110011. doi: 10.1016/j.ecoenv.2019.110011. Epub 2019 Nov 30.
Organophosphate pesticides are widely applied worldwide for agricultural purposes, and their exposures often result in adverse effects on Bombyx mori. The insect gut is a complicated ecosystem inhabited by a large number of microbes that play important roles in insect physiology and behavior. Recent studies have reported that alteration of their microbiota due to stressful conditions or environmental changes has been linked to a compromised health status and a susceptibility to diseases. In the present study, we aimed to assess the effects of phoxim exposure on intestinal microbes in silkworms. The results showed that phoxim exposure increased the bacterial community evenness and altered the structure of gut microbiota in silkworm larvae. The abundances of several genera, such as Methylobacterium and Aurantimonadaceae, in phoxim-treated larval guts were significantly reduced compared with the H2O-treated group, whereas the abundances of non-dominant bacteria, such as Staphylococcus, were significantly increased. Moreover, phoxim inhibited the expressions of antimicrobial peptides (AMPs) at the mRNA level and enhanced the pathogenesis of Enterobacter cloacae (E. cloacae) against silkworm larvae, suggesting that the immune system was inhibited after phoxim exposure. Therefore, the gut microbial community shifts were apparent after phoxim exposure. The compositional and structural changes of intestinal microbes caused by phoxim exposure might affect the normal function of the intestinal tract of silkworm. These results highlighted the importance of the gut bacterial community when investigating the mechanisms of midgut injury after pesticide exposure in Bombyx mori.
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