L-Glufosinate

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L-Glufosinate
Category Enzyme inhibitors
Catalog number BBF-05251
CAS 35597-44-5
Molecular Weight 181.13
Molecular Formula C5H12NO4P
Purity ≥95%

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Description

L-Glufosinate is a glutamine synthetase inhibitor and is used as a herbicide (usually as the corresponding ammonium or sodium salt, known as glufosinate-P-ammonium and glufosinate-P-sodium, respectively) to control annual weeds and grasses.

Specification

Related CAS 70033-13-5 (sodium salt) 73777-50-1 (ammonium salt)
Synonyms Butanoic acid, 2-amino-4-(hydroxymethylphosphinyl)-, (2S)-; Glufosinate-P; (S)-Phosphinothricin; L-Phosphinothricin; (S)-Glufosinate; (+)-glufosinate; L-homoalanin-4-yl(methyl)phosphinic acid; 4-[hydroxy(methyl)phosphinoyl]-L-homoalanine; L-2-Amino-4-(hydroxymethylphosphinyl)butanoate-; (S)-2-Amino-4-(hydroxymethylphosphinyl)butyric acid
Storage Store at -20°C
IUPAC Name (2S)-2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid
Canonical SMILES CP(=O)(CCC(C(=O)O)N)O
InChI InChI=1S/C5H12NO4P/c1-11(9,10)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)(H,9,10)/t4-/m0/s1
InChI Key IAJOBQBIJHVGMQ-BYPYZUCNSA-N

Properties

Application

L-Glufosinate is a compound that has shown promise in the field of drug discovery. With its unique properties and mechanisms of action, it has the potential to be utilized in the development of new pharmaceuticals for various medical conditions.

Phosphinothricin, another name for L-glufosinate, is a derivative of amino acids that functions as a strong herbicide by preventing plants from producing the enzyme glutamine synthetase. Beyond its herbicidal qualities, though, is its use in drug discovery. According to research, L-glufosinate is a good option for pharmaceutical development because of its capacity to influence biological processes.

Treating neurological conditions is one possible use for L-glufosinate in drug research. According to studies, L-glufosinate has the ability to alter central nervous system activity, which suggests that it could be used in the creation of medications to treat diseases including epilepsy, Parkinson's disease, and Alzheimer's disease. Through its impact on neurotransmission and neuronal excitability, L-glufosinate may provide new opportunities for the creation of innovative treatments for various disorders.

L-glufosinate has also being researched for possible uses in the treatment of cancer. L-glufosinate is a good option for the creation of anticancer medications since studies have shown that it may have cytotoxic effects on cancer cells. It may prove to be an important ingredient in the creation of targeted cancer treatments due to its capacity to inhibit glutamine synthetase and interfere with cellular metabolism.

Moreover, L-glufosinate has potential in the realm of antibiotic development as well as drug discovery. The need for innovative antibiotics has increased due to the growing threat that antibiotic resistance poses to public health. Since L-glufosinate has demonstrated antibacterial action against a range of pathogens, it may serve as a platform for the creation of novel antibiotics to fight infections that are resistant to existing medications.
Boiling Point 519.1±45.0°C (Predicted)
Melting Point 209-210°C
Density 1.378±0.06 g/cm3 (Predicted)

Reference Reading

1. Comparison of the chronic and multigenerational toxicity of racemic glufosinate and l-glufosinate to Caenorhabditis elegans at environmental concentrations
Xu Zhao, Kan Fu, Kai-Ping Xiang, Lan-Ying Wang, Yun-Fei Zhang, Yan-Ping Luo Chemosphere. 2023 Mar;316:137863. doi: 10.1016/j.chemosphere.2023.137863. Epub 2023 Jan 14.
Glufosinate-ammonium, the second largest transgene crop resistant herbicide, is classified as a mobile persistent pollutant by the U.S. Environmental Protection Agencybecause of its slow decomposition and easy mobile transfer in a water environment. The chronic and multigeneration toxicity of this compound to environmental organisms are alarming. In this study, racemic glufosinate-ammonium and the effective isomer, l-glufosinate-ammonium, were used as the test agents. The developmental, neurotoxic and reproductive toxicities of Caenorhabditis elegans to their parents and progeny were studied by continuous exposure in water at concentrations of 0.1, 1, 10 and 100 μg/L. The causes of toxicity differences were analysed from oxidative stress and transcription levels. Through oxidative stress of C. elegans, racemic glufosinate-ammonium and l-glufosinate-ammonium both mediated the developmental toxicity (shortened developmental cycle, reduced body length and width, promoted ageingand decreased longevity), neurotoxicity (inhibited head swinging, body bending frequency and acetylcholinesterase [AchE] activity) and reproductive toxicity (significant reductions in the number of eggs and offspring in vivo and induced apoptosis of gonadal cells). These phenomena caused oxidative damage (protein and membrane lipid peroxidation) and further induced apoptosis. The changes in various indicators caused by racemic glufosinate-ammonium exposure were more significant than those caused by l-glufosinate-ammonium exposure, and the reproduction-related indicators were more significant than the developmental and neurological indicators. A continuous accumulation of toxicity was observed after multiple generations of continuous exposure. These research results provide a data reference for the ecotoxicological evaluation and risk assessment of glufosinate-ammonium and contribute to the revision and improvement of the related environmental policies of glufosinate-ammonium.
2. Genetic Analysis and Fine Mapping of ZmGHT1 Conferring Glufosinate Herbicide Tolerance in Maize ( Zea mays L.)
Jianxi Bao, Yuexin Gao, Yanan Li, Suowei Wu, Jinping Li, Zhenying Dong, Xiangyuan Wan Int J Mol Sci. 2022 Sep 29;23(19):11481. doi: 10.3390/ijms231911481.
Weed interference in the crop field is one of the major biotic stresses causing dramatic crop yield losses, and the development of herbicide-resistant crops is critical for weed control in the application of herbicide technologies. To identify herbicide-resistant germplasms, we screened 854 maize inbreed lines and 25,620 seedlings by spraying them with 1 g/L glufosinate. One plant (L336R), possibly derived from a natural variation of line L336, was identified to have the potential for glufosinate tolerance. Genetic analysis validated that the glufosinate tolerance of L336R is conferred by a single locus, which was tentatively designated as ZmGHT1. By constructing a bi-parental population derived from L336R, and a glufosinate sensitive line L312, ZmGHT1 was mapped between molecular markers M9 and M10. Interestingly, genomic comparation between the two sequenced reference genomes showed that large scale structural variations (SVs) occurred within the mapped region, resulting in 2.16 Mb in the inbreed line B73, and 11.5 kb in CML277, respectively. During the fine mapping process, we did not detect any additional recombinant, even by using more than 9500 F2 and F3 plants, suspecting that SVs should also have occurred between L336R and L312 in this region, which inhibited recombination. By evaluating the expression of the genes within the mapped interval and using functional annotation, we predict that the gene Zm00001eb361930, encoding an aminotransferase, is the most likely causative gene. After glufosinate treatment, lower levels of ammonia content and a higher activity of glutamine synthetase (GS) in L336R were detected compared with those of L336 and L312, suggesting that the target gene may participate in ammonia elimination involving GS activity. Collectively, our study can provide a material resource for maize herbicide resistant breeding, with the potential to reveal a new mechanism for herbicide resistance.
3. Comparing toxicity and biodegradation of racemic glufosinate and L-glufosinate in green algae Scenedesmus obliquus
Xiurou Meng, Fei Wang, Yunfang Li, Pengyu Deng, Deyu Hu, Yuping Zhang Sci Total Environ. 2022 Jun 1;823:153791. doi: 10.1016/j.scitotenv.2022.153791. Epub 2022 Feb 9.
Glufosinate-ammonium, a widely used chiral herbicide, has become the focus of attention because of its toxicity toward non-target organisms and its degradation behavior in the environment. With the introduction of L-glufosinate-ammonium products, the toxicity and environmental behavior of rac-glufosinate-ammonium and L-glufosinate-ammonium have become the subject of increasing interest. The overall goal of this study was to investigate the differences in toxicity and biodegradation of rac-glufosinate-ammonium and L-glufosinate-ammonium in an aquatic organism, Scenedesmus obliquus. The toxicity of rac-glufosinate-ammonium and L-glufosinate-ammonium to S. obliquus was compared by measuring EC50, malondialdehyde (MDA) content, protein content and antioxidant enzyme activity. The 96-h EC50 values of rac-glufosinate-ammonium and L-glufosinate-ammonium were 57.22 μg/mL and 25.55 μg/mL, respectively, which indicated that L-glufosinate-ammonium was more toxic to S. obliquus than rac-glufosinate-ammonium. Based on the MDA content, protein content, and antioxidant enzyme (SOD and CAT) activity, we found that L-glufosinate-ammonium could cause more serious oxidative damage than rac-glufosinate-ammonium. The residual amount of glufosinate-ammonium and its metabolites in the culture medium and S. obliquus were determined by HPLC-HRMS. Comparison of glufosinate-ammonium concentrations in algae-free and algae-containing media, showed that glufosinate-ammonium degradation in the S. obliquus system was significantly increased, and the degradation rate of L-glufosinate-ammonium was faster than that of D-glufosinate-ammonium. No enantiomerization was observed for pure L-glufosinate-ammonium treatment. N-acetyl-glufosinate was identified as the main metabolite of glufosinate-ammonium.

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