Cyclo(delta-Ala-L-Val)
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| Category | Others |
| Catalog number | BBF-04220 |
| CAS | 25516-00-1 |
| Molecular Weight | 168.19 |
| Molecular Formula | C8H12N2O2 |
| Purity | >98% by HPLC |
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Description
It is a diketopiperazine formed by the fusion of δ-alanine and valine and is a secondary metabolite of fungi and bacteria. It can activate N-acylhomoserine lactones (AHLs) and can also activate or antagonize other LuxR-based quorum-sensing systems.
Specification
| Synonyms | 3-Methylene-6S-(1-methylethyl)-2,5-piperazinedione; 2,5-Piperazinedione, 3-methylene-6-(1-methylethyl)-, (S)-; Cyclo(Δ-Ala-L-Val) |
| Storage | Store at -20°C |
| IUPAC Name | (6S)-3-methylidene-6-propan-2-ylpiperazine-2,5-dione |
| Canonical SMILES | CC(C)C1C(=O)NC(=C)C(=O)N1 |
| InChI | InChI=1S/C8H12N2O2/c1-4(2)6-8(12)9-5(3)7(11)10-6/h4,6H,3H2,1-2H3,(H,9,12)(H,10,11)/t6-/m0/s1 |
| InChI Key | NFYRGJUKSGFWQF-LURJTMIESA-N |
| Source | Synthetic |
Properties
| Appearance | White Solid |
| Boiling Point | 469.8±45.0°C (Predicted) |
| Density | 1.13±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1. trans-4-(2-Amino-5-bromo-6-methyl-pyrimidin-4-ylamino)-1-methyl-cyclo-hexa-nol
Alex Yanovsky, Arnold L Rheingold, Jacqui E Hoffman, Antonio Dipasquale, Henry Cheng Acta Crystallogr Sect E Struct Rep Online . 2009 Sep 9;65(Pt 10):o2374. doi: 10.1107/S1600536809035533.
The title compound, C(12)H(19)BrN(4)O, represents the minor component of the two products obtained in a series of transformations involving the Grignard reaction of tert-butoxy-carbonyl-protected 4-amino-cyclo-hexa-none with MeMgBr, and subsequent inter-action of the obtained amino-substituted cyclo-hexa-nol with 4-chloro-6-methyl-pyrimidin-2-amine followed by bromination with N-bromo-succinimide. The X-ray structure showed that this product represents a trans isomer with respect to the amino and hydr-oxy substituents in the cyclo-hexyl ring; the dihedral angle between the amino-pyrimidine plane and the (noncrystallographic) mirror plane of the substituted cyclo-hexyl fragment is 33.6 (3)°. Only two of the four potentially 'active' H atoms participate in inter-molecular N-H⋯O and O-H⋯N hydrogen bonds, linking the mol-ecules into layers parallel to the (10) plane.
2. Neuroprotective Effect of Cyclo-(L-Pro-L-Phe) Isolated from the Jellyfish-Derived Fungus Aspergillus flavus
Jee H Jung, Eun La Kim, Ying Wang, Dan-Dan Li, Jongki Hong Mar Drugs . 2021 Jul 26;19(8):417. doi: 10.3390/md19080417.
Peroxisome proliferator-activated receptor (PPAR) expression has been implicated in pathological states such as cancer, inflammation, diabetes, and neurodegeneration. We isolated natural PPAR agonists-eight 2,5-diketopiperazines-from the jellyfish-derived fungusAspergillus flavus. Cyclo-(L-Pro-L-Phe) was the most potent PPAR-γ activator among the eight 2,5-DKPs identified. Cyclo-(L-Pro-L-Phe) activated PPAR-γ in Ac2F rat liver cells and SH-SY5Y human neuroblastoma cells. The neuroprotective effect of this partial PPAR-γ agonist was examined using the 3-(4, 5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay, lactate dehydrogenase release, and the Hoechst 33342 staining assay in SH-SY5Y cells. Our findings revealed that cyclo-(L-Pro-L-Phe) reduced hydrogen peroxide-induced apoptosis as well as the generation of reactive oxygen species. Rhodamine 123 staining and western blotting revealed that cyclo-(L-Pro-L-Phe) prevented the loss of mitochondrial membrane potential and inhibited the activation of mitochondria-related apoptotic proteins, such as caspase 3 and poly (ADP-ribose) polymerase. Moreover, cyclo-(L-Pro-L-Phe) inhibited the activation and translocation of nuclear factor-kappa B. Thus, the partial PPAR-γ agonist cyclo-(L-Pro-L-Phe) demonstrated potential neuroprotective activity against oxidative stress-induced neurodegeneration in SH-SY5Y cells.
3. 11,12-Dihy-droxy-10,6,8,11,13-icetexapentan-1-one
Suchada Chantrapromma, Ibrahim Abdul Razak, Hoong-Kun Fun, Abdul Wahab Salae Acta Crystallogr Sect E Struct Rep Online . 2011 Jan 8;67(Pt 2):o256-7. doi: 10.1107/S1600536810053754.
THE TITLE COMPOUND [SYSTEMATIC NAME: 14,15-dihy-droxy-7,7-dimethyl-13-(propan-2-yl)tricyclo-[9.4.0.0(3,8)]penta-deca-1(11),3(8),9,12,14-pentaen-4-one], C(20)H(24)O(3), is a new icetexane diterpenoid which was isolated from the roots of Premna obtusifolia (Verbenaceae). The mol-ecule has three fused rings: a cyclo-hexenone, a central cyclo-heptene and a benzene ring. The cyclo-hexenone ring is in an envelope conformation, whereas the cyclo-heptene ring is in a twisted boat conformation. Intra-molecular O-H⋯O hydrogen bonds generate S(5) and S(8) ring motifs. In the crystal, mol-ecules are linked into dimers through O-H⋯O hydrogen bonds. These dimers are arranged in to sheets parallel to the ac plane. C-H⋯O and weak C-H⋯π inter-actions are also present.
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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 ╳
