Eurystatin B
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00884 |
| CAS | 137563-64-5 |
| Molecular Weight | 464.60 |
| Molecular Formula | C24H40N4O5 |
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Description
Eurystatin B is a prolyl endopeptidase inhibitor produced by Streptomyces eyrythermus R353-21.
Specification
| Synonyms | 2-Octenamide, 6-methyl-N-(7-methyl-3-(2-methylpropyl)-2,5,6,9-tetraoxo-1,4,8-triazacyclotridec-10-yl)- |
| IUPAC Name | (E)-6-methyl-N-[7-methyl-3-(2-methylpropyl)-2,5,6,9-tetraoxo-1,4,8-triazacyclotridec-10-yl]oct-2-enamide |
| Canonical SMILES | CCC(C)CCC=CC(=O)NC1CCCNC(=O)C(NC(=O)C(=O)C(NC1=O)C)CC(C)C |
| InChI | InChI=1S/C24H40N4O5/c1-6-16(4)10-7-8-12-20(29)27-18-11-9-13-25-22(31)19(14-15(2)3)28-24(33)21(30)17(5)26-23(18)32/h8,12,15-19H,6-7,9-11,13-14H2,1-5H3,(H,25,31)(H,26,32)(H,27,29)(H,28,33)/b12-8+ |
| InChI Key | YNIGBMUXBCZRNQ-XYOKQWHBSA-N |
Properties
| Appearance | Colorless Crystal |
| Melting Point | 291-293°C(dec.) |
| Density | 1.12 g/cm3 |
Reference Reading
1. Eurystatins A and B, new prolyl endopeptidase inhibitors. III. Fermentation and controlled biosynthesis of eurystatin analogs by Streptomyces eurythermus
K Suzuki, S Toda, T Furumai, Y Fukagawa, T Oki J Antibiot (Tokyo). 1994 Sep;47(9):982-91. doi: 10.7164/antibiotics.47.982.
Accurate and precise component analysis of eurystatin analogs in fermentation broth was devised by HPLC methods with and without 2,4-dinitrophenylhydrazonation. Detailed optimization of fermentation conditions and strain improvement by HPLC analysis significantly increased the eurystatin productivity of Streptomyces eurythermus. Chemically defined fermentation media which produced eurystatins A and B at fermentation yields comparable to complex media were elaborated for radio-isotope fermentation studies and controlled biosynthesis. Radio-isotope incorporation study using 14C-labeled amino acids in chemically defined medium demonstrated that L-leucine and L-ornithine were the direct precursors for the L-leucine and L-ornithine moieties of eurystatins A and B, respectively. Based on this finding, L-valine and L-isoleucine were supplemented to the growing culture of S. eurythermus in chemically defined medium, which resulted in the controlled biosynthesis of new eurystatin analogs named eurystatins C, D, E and F.
2. Eurystatins A and B, new prolyl endopeptidase inhibitors. I. Taxonomy, production, isolation and biological activities
S Toda, Y Obi, K Numata, Y Hamagishi, K Tomita, N Komiyama, C Kotake, T Furumai, T Oki J Antibiot (Tokyo). 1992 Oct;45(10):1573-9. doi: 10.7164/antibiotics.45.1573.
Eurystatins A and B, were isolated from the cultured broth of Streptomyces eurythermus R353-21. They showed specific and potent inhibitory activity against prolyl endopeptidase and did not show antimicrobial activity. No lethal toxicity was observed for the two compounds after ip administration in mice at 200 mg/kg.
3. Eurystatins A and B, new prolyl endopeptidase inhibitors. II. Physico-chemical properties and structure determination
S Toda, C Kotake, T Tsuno, Y Narita, T Yamasaki, M Konishi J Antibiot (Tokyo). 1992 Oct;45(10):1580-6. doi: 10.7164/antibiotics.45.1580.
The structures of eurystatins A and B, new prolyl endopeptidase inhibitors, have been elucidated by chemical degradation and spectral studies. They have in common a unique 13-membered cyclic peptide core composed of L-leucine, L-ornithine and (S)-3-amino-2-oxobutyric acid, and differ from each other in the alpha,beta-unsaturated fatty acid attached to the alpha-amino moiety of the ornithine.
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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 ╳
