Cyclopeptine
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| Category | Others |
| Catalog number | BBF-04219 |
| CAS | 50886-63-0 |
| Molecular Weight | 280.32 |
| Molecular Formula | C17H16N2O2 |
| Purity | >99% by HPLC |
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Description
A benzodiazepine metabolite produced by a number of species of penicillium.
Specification
| Synonyms | (S)-cyclopeptine; (3S)-3-benzyl-4-methyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione |
| Storage | Store at -20°C |
| IUPAC Name | (3S)-3-benzyl-4-methyl-1,3-dihydro-1,4-benzodiazepine-2,5-dione |
| Canonical SMILES | CN1C(C(=O)NC2=CC=CC=C2C1=O)CC3=CC=CC=C3 |
| InChI | InChI=1S/C17H16N2O2/c1-19-15(11-12-7-3-2-4-8-12)16(20)18-14-10-6-5-9-13(14)17(19)21/h2-10,15H,11H2,1H3,(H,18,20)/t15-/m0/s1 |
| InChI Key | KSQNKZMAMGACTL-HNNXBMFYSA-N |
| Source | Penicillium sp. |
Properties
| Appearance | Colorless Solid |
| Boiling Point | 514.3±43.0°C (Predicted) |
| Melting Point | 95-98°C |
| Density | 1.206±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1. Cyclopeptide alkaloids: chemistry and biology
David J Richard, Madeleine M Joullié Chem Commun (Camb) . 2004 Sep 21;(18):2011-5. doi: 10.1039/b400334a.
Recent progress in the synthesis and investigation of the biological activities of cyclopeptide alkaloids is reviewed. New strategies have been devised to overcome some of the synthetic challenges inherent in the formation of strained paracyclophanes. However, issues remain which offer opportunities for the application of catalytic enantioselective organometallic reactions. Members of this class of natural products have been isolated from various parts of a wide variety of plants and researchers will likely continue to show great interest in their formation and function. The biological properties of certain members of this class warrant further investigation. To gain additional insight into these areas, continuing development of synthetic methodology will be essential.
2. Cyclopeptide Derivatives from the Sponge-Derived Fungus Acremonium persicinum F10
Yingxin Li, Zhiyong Li Mar Drugs . 2021 Sep 24;19(10):537. doi: 10.3390/md19100537.
Cyclopeptides usually play a pivotal role, either in the viability or virulence of fungi. Two types of cyclopeptides, six new hydroxamate siderophore cyclohexapeptides (1-6), including acremonpeptides E and F, and their complexes with aluminum and ferric ions; one new cyclic pentapeptolide, aselacin D (9); together with a known compound, aselacin C (10), were isolated and characterized from the sponge-derived fungusAcremonium persicinumF10. In addition, two new siderophore analogues chelating gallium ions (Ga3+), Ga (III)-acremonpeptide E (7) and Ga (III)-acremonpeptide F (8), using isolated acremonpeptides E and F, were prepared. The planar structures of1-10were elucidated by HRESIMS and (1D and 2D) NMR. The absolute configurations of amino acids were determined by means of the advanced Marfey's method and X-ray single-crystal diffraction analysis. X-ray fluorescence (XRF) spectrometer was performed to disclose the elements of compound1, indicating the existence of aluminum (Al). Al (III)-acremonpeptides E (1), Ga (III)-acremonpeptides E (5), Al (III)-acremonpeptide F (7), and Ga (III)-acremonpeptide F (8) displayed high in vitro anti-fungal activities, which are comparable to amphotericin B, againstAspergillus fumigatusandAspergillus niger.
3. Approaches to Cyclophane-Types of Cyclopeptide Alkaloids
Yuanhao Wang, Madeleine M Joullié Chem Rec . 2021 Apr;21(4):906-923. doi: 10.1002/tcr.202100017.
The cyclopeptide alkaloids are cyclic depsipeptides incorporating cyclophanes with polyamide units 13-, 14- and 15-membered macrocyclic systems. Although various pharmacological activities have been ascribed to cyclopeptide alkaloids from plants of the Rhamnacea family, these studies have been hampered by their low availability due to the lack of reasonable amounts distributed in nature. Therefore, novel and efficient synthetic approaches should be an important aim, which inspired us to examine how to diversely construct the unique structures of this type of natural products. In this account, several typical strategies are presented in terms of efficient, stereocontrolled and regioselective synthesis of cyclopeptide alkaloids.
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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 ╳
