EI-2128-1
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| Category | Antibiotics |
| Catalog number | BBF-02815 |
| CAS | |
| Molecular Weight | 421.53 |
| Molecular Formula | C23H35NO6 |
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Description
EI-2128-1 is originally isolated from Penicillum sp. E-2128. It selectively inhibited ICE, and the IC50 of recombinant human ICE was 0.59 μmol/L. It also has anti-Gram-positive bacteria such as Bacillus subtilis, Staphylococcus aureus and Enterococcus enterococcus.
Specification
| Synonyms | (2E)-N-[(1R,3S,4'S,5R,5'R,7S)-5'-Hydroxy-6-oxodihydro-3'H-spiro[4,8-dioxatricyclo[5.1.0.03,5]octane-2,2'-furan]-4'-yl]-4,6-dimethyl-2-dodecenamide |
| IUPAC Name | (E)-N-[(1R,2'R,3S,3'S,5R,7S)-2'-hydroxy-6-oxospiro[4,8-dioxatricyclo[5.1.0.03,5]octane-2,5'-oxolane]-3'-yl]-4,6-dimethyldodec-2-enamide |
| Canonical SMILES | CCCCCCC(C)CC(C)C=CC(=O)NC1CC2(C3C(O3)C(=O)C4C2O4)OC1O |
| InChI | InChI=1S/C23H35NO6/c1-4-5-6-7-8-13(2)11-14(3)9-10-16(25)24-15-12-23(30-22(15)27)20-18(28-20)17(26)19-21(23)29-19/h9-10,13-15,18-22,27H,4-8,11-12H2,1-3H3,(H,24,25)/b10-9+/t13?,14?,15-,18-,19+,20-,21+,22+,23?/m0/s1 |
| InChI Key | VUFZKMYXIBBYJI-XZFFCROKSA-N |
Properties
| Appearance | White Powder |
| Boiling Point | 633.1±55.0°C at 760 mmHg |
| Density | 1.2±0.1 g/cm3 |
Reference Reading
1. EI-2128-1, a novel interleukin-1beta converting enzyme inhibitor produced by Penicillium sp. E-2128
Fumito Koizumi, Tsutomu Agatsuma, Katsuhiko Ando, Hidemasa Kondo, Yutaka Saitoh, Yuzuru Matsuda, Satoshi Nakanishi J Antibiot (Tokyo). 2003 Nov;56(11):891-8. doi: 10.7164/antibiotics.56.891.
EI-2128-1, a novel interleukin-1beta converting enzyme (ICE) inhibitor, was isolated from the culture broths of Penicillium sp. E-2128. EI-2128-1 selectively inhibited human recombinant ICE activity with IC50 value of 0.59 microM, without inhibiting elastase and cathepsin B. EI-2128-1 also inhibited mature interleukin-1beta secretion from THP-1 cells induced by LPS with IC50 value of 0.28 microM.
2. Total Synthesis and Structural Reassignment of Aranorosinol A, Aranorosinol B, and EI-2128-1
Haiyong Yu, Yingyuan Tian, Yan Zong, Jianyu Zhang, Tao Xu J Org Chem. 2020 Mar 20;85(6):4335-4343. doi: 10.1021/acs.joc.0c00028. Epub 2020 Mar 6.
Herein, we report a concise and collective total synthesis of three natural products aranorosinol A, aranorosinol B, and EI-2128-1 and also the known penicimutanolone. A unified strategy was conceived, which divergently accessed all four congeners within 9-11 steps (LLS) from a common intermediate. Bisoxirane-directed 1,2-addition was utilized as a key step to generate the desired configuration of the C8 stereocenter of aranorosinol A and B, 28 years after their first isolation, and these were both assigned as S configurations, while the C4' and C6' configurations of EI-2128-1 were both determined to be R,R-configurations.
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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 ╳
