Penta-N-acetylchitopentaose
(Synonyms: N,N',N,N''',N-五乙酰壳五糖) 目录号 : GC44595
A chito-oligosaccharide involved in root nodulation
Cas No.:36467-68-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Root nodules, like those induced on the roots of leguminous plants by Rhizobium bacteria, are important sites for the conversion of atmospheric nitrogen into ammonia. The initiation and development of these growths are driven by a variety of nodulation (Nod) proteins produced by the infecting bacteria. Penta-N-acetylchitopentaose is a pentameric chito-oligosaccharide involved in nodulation. It can be produced by NodC, a chito-oligosaccharide synthase, and serve as a substrate for NodL, an O-acetyltransferase. This bacterial product binds plant root lectins, and this interaction may be important in the promotion of cell division in the root cortex. Penta-N-acetylchitopentaose, as well as chitin and chitosan, inhibits nitric oxide production in LPS-activated RAW 264.7 macrophages.
| Cas No. | 36467-68-2 | SDF | |
| 别名 | N,N',N,N''',N-五乙酰壳五糖 | ||
| Canonical SMILES | O[C@@H]1[C@@H](CO)O[C@](O[C@@H]2[C@@H](CO)O[C@](O[C@H]3[C@H](O)[C@@H](NC(C)=O)[C@H](O[C@]4([H])[C@@H](CO)O[C@@H](O[C@@]([C@H](O)CO)([H])[C@H](O)C(NC(C)=O)C=O)[C@H](NC(C)=O)[C@H]4O)O[C@@H]3CO)([H])[C@H](NC(C)=O)[C@H]2O)([H])[C@H](NC(C)=O)[C@H]1O | ||
| 分子式 | C40H67N5O26 | 分子量 | 1034 |
| 溶解度 | PBS (pH 7.2): 1 mg/ml | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 0.9671 mL | 4.8356 mL | 9.6712 mL |
| 5 mM | 0.1934 mL | 0.9671 mL | 1.9342 mL |
| 10 mM | 0.0967 mL | 0.4836 mL | 0.9671 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Experimental Measurements and Mathematical Modeling of Cytosolic Ca(2+) Signatures upon Elicitation by Penta-N-acetylchitopentaose Oligosaccharides in Nicotiana tabacum Cell Cultures
Plants (Basel) 2013 Nov 27;2(4):750-68.PMID:27137402DOI:10.3390/plants2040750.
Plants have developed sophisticated recognition systems for different kinds of pathogens. Pathogen-associated molecular patterns (PAMPs) can induce various defense mechanisms, e.g., the production of reactive oxygen species (ROS) as an early event. Plant defense reactions are initiated by a signal transduction cascade involving the release of calcium ions (Ca(2+)) from both external and internal stores to the plant cytoplasm. This work focuses on the analysis of cytosolic Ca(2+) signatures, experimentally and theoretically. Cytosolic Ca(2+) signals were measured in Nicotiana tabacum plant cell cultures after elicitation with Penta-N-acetylchitopentaose oligosaccharides (Ch5). In order to allow a mathematical simulation of the elicitor-triggered C(a2)+ release, the Li and Rinzel model was adapted to the situation in plants. The main features of the Ca2+ response, like the specific shape of the C(a2)+ transient and the dose-response relationship, could be reproduced very well. Repeated elicitation of the same cell culture revealed a refractory behavior with respect to the Ca(2+) transients for this condition. Detailed analysis of the obtained data resulted in further modifications of the mathematical model, allowing a predictive simulation of Ch5-induced C(a2)+ transients. The promising results may contribute to a deeper understanding of the underlying mechanisms governing plant defense.
Concise synthesis of 4-methylumbelliferyl-penta-N-acetylchitopentaoside and its inhibition effect on chitinase
Int J Biol Macromol 2009 Nov 1;45(4):381-3.PMID:19635498DOI:10.1016/j.ijbiomac.2009.07.002.
The synthesis of 4-methylumbelliferyl (UMB)-penta-N-acetylchitopentaoside 4 and its inhibition effect on chitinase are described. The fluorophore-assisted carbohydrate electrophoresis (FACE) analysis showed that the partially N-acetylated chitooligosaccharide (COS) mixture mainly contained glucosamine (GlcN) and oligomers [(GlcN)n, n=2-7]. The peracetylated COSs [(GlcNAc)(n), n=1-7] were synthesized by treating the partially N-acetylated COS mixture with Ac2O-NaOAc. The peracetylated chitopentaoside 1 was obtained by isolation of peracetylated COS mixture. The peracetylated UMB chitopentaoside 3 was synthesized by treating compound 1 with 4-methylumbelliferone and a Lewis acid (SnCl4) catalyst. NaOMe in dry methanol was used for deacetylation of the blocked derivative, to give the target compound 4 in an overall yield of 32%. In binding chitinase assay, it indicates that compound 4 is much more stable than the corresponding Penta-N-acetylchitopentaose 2.
Structural and biochemical insights into an insect gut-specific chitinase with antifungal activity
Insect Biochem Mol Biol 2020 Apr;119:103326.PMID:31968227DOI:10.1016/j.ibmb.2020.103326.
The antifungal activity of insect chitinase has rarely been studied. Here, we show that chitinase ChtIV, which is specifically expressed in the midgut of Asian corn borer (Ostrinia furnacalis), has antifungal activity toward phytopathogenic fungi. ChtIV exhibited high stability and mycelial hydrolytic activity in the extreme midgut environment, which has a pH of 10 and is rich in proteases. Hyper-N-glycosylation and reduced electrostatic interactions ensure the stability of ChtIV in the midgut. The structural characteristics of ChtIV are similar to two plant antifungal chitinases but distinct from an insect chitinase for cuticular chitin degradation in both the substrate-binding cleft and auxiliary binding motif. Since the phytopathogenic fungi are those that frequently invade corn, ChtIV may play a role in insect immune system and become a potential pesticide target. The crystal structures of ChtIV and its complexes with Penta-N-acetylchitopentaose (a substrate) and allosamidin (an inhibitor) were obtained, which may facilitate rational design of ChtIV inhibitors as agrichemicals.
Induced accumulation of 2-hydroxy-4,7-dimethoxy-1,4-benzoxazin-3-one glucoside (HDMBOA-Glc) in maize leaves
Phytochemistry 2001 Apr;56(7):669-75.PMID:11314951DOI:10.1016/s0031-9422(00)00494-5.
Accumulation of 2-(2-hydroxy-4,7-dimethoxy-1,4-benzoxazin-3-one)-beta-D-glucopyranose (HDMBOA-Glc) was induced in maize leaves by treatment with CuCl2, chitopentaose, Penta-N-acetylchitopentaose, or jasmonic acid (JA). The accumulation of HDMBOA-Glc was accompanied by a decrease in level of 2-(2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one)-beta-D-glucopyranose (DIMBOA-Glc). When the leaf segments were treated with JA in the presence of [Me-2H3]L-methionine, the label was efficiently incorporated into HDMBOA-Glc, while no incorporation into DIMBOA-Glc or HMBOA-Glc was detected, suggesting the conversion of constitutive DIMBOA-Glc to HDMBOA-Glc by methylation at the 4-position. Levels of endogenous JA and its leucine conjugate transiently increased prior to the accumulation of HDMBOA-Glc in leaf segments treated with CuCl2 and chitopentaose. The lipoxygenase inhibitor ibuprofen suppressed the accumulation of HDMBOA-Glc induced by CuCl2 treatment, and the reduced accumulation of HDMBOA-Glc was recovered by addition of JA. These findings suggested that JA functions as a signal transducer in the induction of HDMBOA-Glc accumulation.
[Biosynthesis of chitooligosaccharides by recombinant Escherichia coli]
Sheng Wu Gong Cheng Xue Bao 2007 May;23(3):525-9.PMID:17578006doi
Acetyl-N-glucosaminyltransferase gene (nodC) was successfully cloned to Escherichia coli from Mesorhizobium loti. The recombinant E. coli harboring nodC gene was able to synthesize chitooligosaccharides (COs) in MMYNG medium. In optimized condition, a yield of 526 mg/L was obtained after 26 h cultivation in 10 L bioreactor. COs concentration reached up to 4.5% of the cell dry weight. The COs products were purified by charcoal adsorption and Bio-gel P4 chromatography, Penta-N-acetylchitopentaose (m/z, 1034[M + H]+) and tetra-N-acetylchitopentaose (m/z, 831 [M + H]+) were identified as the dominating COs product using the method of liquid chromatography-electrospray ionization mass spectrometry (LC-ESI-MS).