Unguisin A
目录号 : GC45119
A cyclic heptapeptide containing GABA
Cas No.:226956-06-5
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
Unguisin A is a cyclic heptapeptide originally isolated from the marine fungus E. unguis whose structure is comprised of amino acids and GABA. It binds to phosphate, pyrophosphate, and chloride but has no effect on chloride transport in a liposome-based assay. It exhibited moderate antibacterial activity against S. aureus and V. parahaemolyticus in one assay but no activity against a variety of bacteria, including S. aureus, in another.
| Cas No. | 226956-06-5 | SDF | |
| Canonical SMILES | O=C(NCCCC(N[C@H](C)C1=O)=O)[C@@H](CC2=CNC3=CC=CC=C32)NC([C@@H](C)NC([C@](C(C)C)([H])NC([C@H](CC4=CC=CC=C4)NC([C@@H](C(C)C)N1)=O)=O)=O)=O | ||
| 分子式 | C40H54N8O7 | 分子量 | 758.9 |
| 溶解度 | DMF: soluble,DMSO: soluble,Ethanol: soluble,Methanol: soluble | 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 | 1.3177 mL | 6.5885 mL | 13.177 mL |
| 5 mM | 0.2635 mL | 1.3177 mL | 2.6354 mL |
| 10 mM | 0.1318 mL | 0.6588 mL | 1.3177 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。
Cyclic peptide Unguisin A is an anion receptor with high affinity for phosphate and pyrophosphate
Org Biomol Chem 2017 Apr 5;15(14):2962-2967.PMID:28294280DOI:10.1039/c7ob00316a.
Unguisin A (1) is a marine-derived, GABA-containing cyclic heptapeptide. The biological function of this flexible macrocycle is obscure. Here we show that compound 1 lacks any detectable activity in antimicrobial growth inhibition assays, a result that runs contrary to a previous report. However, we find that 1 functions as a promiscuous host molecule in a variety of anion-binding interactions, with high affinity particularly for phosphate and pyrophosphate. We also show that a series of rigidified, backbone-fluorinated analogues of 1 displays altered affinity for chloride ions.
Understanding the Conformational Properties of Fluorinated Polypeptides: Molecular Modelling of Unguisin A
J Chem Inf Model 2021 Jan 25;61(1):223-237.PMID:33325701DOI:10.1021/acs.jcim.0c00746.
In this work, we investigate the conformational properties of Unguisin A, a natural macrocyclic heptapeptide that incorporates a γ-aminobutyric acid (Gaba), and four of its difluorinated stereoisomers at the Gaba residue. According to nuclear magnetic resonance (NMR) experiments, their secondary structure depends dramatically on the stereochemistry of the fluorinated carbon atoms. However, many molecular details of the structure and flexibility of these systems remain unknown, so that a rationale of the conformational changes induced by the fluorine atoms in the macrocycle is still missing. To fill this gap, we apply enhanced molecular dynamics (MD) techniques to explore the peptide conformational space in dimethyl sulfoxide solution followed by 4-8 μs of conventional MD simulations that provide extensive equilibrium sampling. The simulations, which compare reasonably well with the NMR-based observations, show that the secondary structure of the macrocycle is altered substantially upon fluorination, except for the (S,S) diastereomer. It also turns out that the conformations of the fluorinated peptides are visited during the enhanced MD simulation of natural Unguisin A, suggesting thus that conformations accessible to the unsubstituted macrocyclic peptide may be selected by fluorination. Therefore, computational characterization of the macrocyclic peptides could be helpful in the rational design of stereoselective fluorinated peptides with fine-tuned conformation and activity.
Total synthesis of Unguisin A
J Org Chem 2011 Jul 1;76(13):5502-5.PMID:21612288DOI:10.1021/jo200813a.
The first synthesis of the γ-aminobutyric acid (GABA)-containing cyclic heptapeptide Unguisin A is reported, confirming the structure of this natural product. Macrocyclization of a flexible GABA-containing linear precursor is found to proceed rapidly and in good yield.
Nitrogen-Containing Secondary Metabolites from a Deep-Sea Fungus Aspergillus unguis and Their Anti-Inflammatory Activity
Mar Drugs 2022 Mar 20;20(3):217.PMID:35323515DOI:10.3390/md20030217.
Aspergillus is well-known as the second-largest contributor of fungal natural products. Based on NMR guided isolation, three nitrogen-containing secondary metabolites, including two new compounds, variotin B (1) and coniosulfide E (2), together with a known compound, Unguisin A (3), were isolated from the ethyl acetate (EtOAc) extract of the deep-sea fungus Aspergillus unguis IV17-109. The planar structures of 1 and 2 were elucidated by an extensive analysis of their spectroscopic data (HRESIMS, 1D and 2D NMR). The absolute configuration of 2 was determined by comparison of its optical rotation value with those of the synthesized analogs. Compound 2 is a rare, naturally occurring substance with an unusual cysteinol moiety. Furthermore, 1 showed moderate anti-inflammatory activity with an IC50 value of 20.0 µM. These results revealed that Aspergillus unguis could produce structurally diverse nitrogenous secondary metabolites, which can be used for further studies to find anti-inflammatory leads.
Stereoselective fluorination alters the geometry of a cyclic peptide: exploration of backbone-fluorinated analogues of Unguisin A
Angew Chem Int Ed Engl 2014 Jun 10;53(24):6176-9.PMID:24848423DOI:10.1002/anie.201403071.
New methods for enhancing the efficiency of peptide cyclization, and for fine-tuning the conformations of cyclic peptides, are valuable from a drug development perspective. Herein stereoselective fluorination is investigated as a new strategy for achieving these goals. Four vicinal difluorinated analogues of the natural cyclic heptapeptide Unguisin A have been efficiently synthesized. The analogues are found to adopt dramatically different secondary structures, controlled by the fluorine stereochemistry.