Cyclo(L-Pro-L-Val)
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| Category | Others |
| Catalog number | BBF-04349 |
| CAS | 2854-40-2 |
| Molecular Weight | 196.25 |
| Molecular Formula | C10H16N2O2 |
| Purity | >98% by HPLC |
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Description
A diketopiperazine derivative isolated from Bacillus thuringiensis and Bacillus endophyticus. It is a secondary metabolite found in various marine fungi and bacteria. It is capable of activating N-acylhomoserine lactones (ahls), also capable of activating or antagonizing other luxr-based quorum-sensing systems.
Specification
| Synonyms | (3S-trans)-Hexahydro-3-(1-methylethyl)-pyrrolo[1,2-a]pyrazine-1,4-dione; (S,S)-Hexahydro-3-isopropyl-pyrrolo[1,2-a]pyrazine-1,4-dione; (-)-(6S,9S)-Cyclo(prolylvalyl); Cyclo(L-Val-L-Pro); Cyclo(L-prolyl-L-valine); Cyclo(L-prolyl-L-valyl); L-Valyl-L-prolyl lactam; Maculosin 5 |
| Storage | Store at 2-8°C |
| IUPAC Name | (3S,8aS)-3-propan-2-yl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione |
| Canonical SMILES | CC(C)C1C(=O)N2CCCC2C(=O)N1 |
| InChI | InChI=1S/C10H16N2O2/c1-6(2)8-10(14)12-5-3-4-7(12)9(13)11-8/h6-8H,3-5H2,1-2H3,(H,11,13)/t7-,8-/m0/s1 |
| InChI Key | XLUAWXQORJEMBD-YUMQZZPRSA-N |
| Source | Synthetic |
Properties
| Appearance | White to Off-white Solid |
| Boiling Point | 420.7±34.0°C (Predicted) |
| Melting Point | 188-192°C |
| Density | 1.17±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO, Chloroform |
Reference Reading
1. Isolation and Structure Identification of Novel Brominated Diketopiperazines from Nocardia ignorata-A Lichen-Associated Actinobacterium
Jean-Pierre Hurvois, Solenn Ferron, Alba Noël, Nicolas Gouault, Isabelle Rouaud, Sophie Tomasi Molecules . 2017 Feb 28;22(3):371. doi: 10.3390/molecules22030371.
Actinobacteria are well known for their potential in biotechnology and their production of metabolites of interest. Lichens are a promising source of new bacterial strains, especially Actinobacteria, which afford a broad chemical diversity. In this context, the culture medium of the actinobacteriumNocardia ignorata,isolated from the terrestrial lichenCollema auriforme, was studied. The strain was cultivated in a BioFlo 115 bioreactor, and the culture medium was extracted using an XAD7HP resin. Five known diketopiperazines: cyclo (l-Pro-l-OMet) (1), cyclo (l-Pro-l-Tyr) (2), cyclo (d-Pro-l-Tyr) (3), cyclo (l-Pro-l-Val) (4), cyclo (l-Pro-l-Leu) (5), and one auxin derivative: indole-carboxaldehyde (8) were isolated, along with two new brominated diketopiperazines: cyclo (d-Pro-l-Br-Tyr) (6) and cyclo (l-Pro-l-Br-Tyr) (7). Structure elucidation was performed using HRMS and 1D and 2D NMR analysis, and the synthesis of compounds6and7was carried out in order to confirm their structure.
2. 2, 5-diketopiperazines (cyclic dipeptides) in beef: identification, synthesis, and sensory evaluation
L Trinnaman, K Kraut, N C Da Costa, D Merritt, L Reiber, M L Dewis, M Z Chen J Food Sci . 2009 Mar;74(2):C100-5. doi: 10.1111/j.1750-3841.2009.01062.x.
Stewed beef and grilled dry aged beef were analyzed as part of an in-depth analytical program, with the aim of creating new flavors incorporating only compounds identified in the target foods and identifying new synthesis targets. In-house GC-MS analyses of several types of cooked beef have identified over 1000 volatile and semivolatile components; many for the 1st time. Among the semivolatiles detected were ten 2, 5-diketopiperazines (cyclic dipeptides) previously unreported in beef. These cyclic dipeptides are cis-cyclo(L-Ile-L-Pro), cis-cyclo(L-Leu-L-Pro), cis-cyclo(L-Pro-L-Pro), cis-cyclo(L-Pro-L-Val), cis-cyclo(L-Ala-L-Pro), cyclo(Gly-L-Pro), cyclo(Gly-L-Leu), cis-cyclo(L-Met-L-Pro), cis-cyclo(L-Phe-L-Pro), and cis-cyclo(L-Phe-L-Val). All 10 cyclic dipeptides were synthesized and evaluated organoleptically. Among them cis-cyclo(L-Leu-L-Pro), cis-cyclo(L-Met-L-Pro), and cis-cyclo(L-Phe-L-Pro) were found to be of particular organoleptic interest.
3. New cytotoxic furan from the marine sediment-derived fungi Aspergillus niger
Ludwig H Pfenning, Barbara S F Rodrigues, Antonia T A Pimenta, Diego V Wilke, Paula Karina S Uchoa, Katharine G D Florêncio, Natália N Saraiva, Mary Anne S Lima, Raimundo Braz-Filho, Maria da Conceição F de Oliveira, Lucas M Abreu Nat Prod Res . 2017 Nov;31(22):2599-2603. doi: 10.1080/14786419.2017.1283499.
A fungal strain of Aspergillus niger was recovered from sediments collected in the Northeast coast of Brazil (Pecém's offshore port terminal). Cultivation in different growth media yielded a new ester furan derivative, 1, along with malformin A1, malformin C, cyclo (trans-4-hydroxy-L-Pro-L-Leu), cyclo (trans-4-hydroxy-L-Pro-L-Phe), cyclo (L-Pro-L-Leu), cyclo (L-Pro-L-Phe), pseurotin D, pseurotin A, chlovalicin, cyclo (L-Pro-L-Tyr) and cyclo (L-Pro-L-Val). Compound 1 was cytotoxic against HCT-116 cell line, showing IC50= 2.9 μg/mL (CI 95% from 1.8 to 4.7 μg/mL).
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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 ╳
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