Esterastin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01704 |
| CAS | 67655-93-0 |
| Molecular Weight | 506.67 |
| Molecular Formula | C28H46N2O6 |
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Description
Esterastin is a lipase inhibitor produced by Streptomyces lavendulae MD4-C1.
Specification
| Synonyms | [(2S,4Z,7Z)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]trideca-4,7-dien-2-yl] (2S)-2-acetamido-4-amino-4-oxobutanoate |
| IUPAC Name | 1-(3-hexyl-4-oxooxetan-2-yl)trideca-4,7-dien-2-yl 2-acetamido-4-amino-4-oxobutanoate |
| Canonical SMILES | CCCCCCC1C(OC1=O)CC(CC=CCC=CCCCCC)OC(=O)C(CC(=O)N)NC(=O)C |
| InChI | InChI=1S/C28H46N2O6/c1-4-6-8-10-11-12-13-14-15-17-22(35-28(34)24(20-26(29)32)30-21(3)31)19-25-23(27(33)36-25)18-16-9-7-5-2/h11-12,14-15,22-25H,4-10,13,16-20H2,1-3H3,(H2,29,32)(H,30,31) |
| InChI Key | JKNGELGDDBUFHG-UHFFFAOYSA-N |
Properties
| Appearance | Colorless Powder |
| Boiling Point | 713.4°C at 760 mmHg |
| Melting Point | 99-100°C |
| Density | 1.058 g/cm3 |
Reference Reading
1. Belactins A and B, new serine carboxypeptidase inhibitors produced by Actinomycete. II. Physico-chemical properties, structure determinations and enzymatic inhibitory activities compared with other beta-lactone containing inhibitors
Y Takahashi, T Aoyagi, S Murakami, T Takeuchi, H Naganawa J Enzyme Inhib . 1995;9(4):277-84. doi: 10.3109/14756369509036556.
Belactins A and B, new inhibitors of serine carboxypeptidase were discovered in the fermentation broth of Saccharopolyspora sp. MK19-42F6. The structures of belactins A and B were determined to be 4-[3-[(2-amino-5-chlorobenzoyl)amino]-1,1-dimethyl-2-oxobutyl]-3- methyl-2-oxetanone and 4-[3-[[2-(beta-glucopyranosylamino)-5-chlorobenzoyl]amino]-1,1- dimethyl-2-oxobutyl]-3-methyl-2-oxetanone respectively by various spectral analyses. Belactins A and B do not inhibit esterase or lipase at 100 micrograms/ml but have more specific inhibitory activities towards carboxypeptidase Y (CP-Y) compared with other beta-lactone-containing inhibitors, such as ebelactones A, B and esterastin.
2. Panclicins, novel pancreatic lipase inhibitors. II. Structural elucidation
Y Itezono, K Yokose, T Ohtsuka, J Watanabe, K Yoshinari, M Aoki, N Nakayama, M Mutoh J Antibiot (Tokyo) . 1994 Dec;47(12):1376-84. doi: 10.7164/antibiotics.47.1376.
Panclicins A-E are novel and potent pancreatic lipase inhibitors produced by Streptomyces sp. NR 0619. Their structures have been elucidated based on NMR and FAB-MS experiments. The relative configurations have also been determined by NMR experiments. The absolute stereochemistry has been determined by the chiral HPLC analysis of the hydrolysates of panclicins A and B and by modified Mosher's method on a derivative of panclicin A. They are structurally related to beta-lactone esterase inhibitors of microbial origin, lipstatin, valilactone, ebelactones and esterastin. Panclicins also contain a beta-lactone structure with two alkyl chains, one of which has an N-formylalanyloxy or N-formylglycyloxy substituent.
3. Effect of esterastin, an acid lipase inhibitor, on the free and esterified cholesterol contents of cultured aortic smooth muscle cells treated with LDL and cholesterol ester liquid crystals
T Aoyagi, T Takano, K Amanuma, G G Ecsedi, T Imanaka, S Ohkuma Biochem Int . 1985 Mar;10(3):337-42.
The effects of esterastin, an acid lipase inhibitor, on the free and esterified cholesterol contents of cultured smooth muscle cells from pig aorta were examined. The post-nuclear supernatant fraction of the cell homogenate showed maximum acid cholesterol esterase activity at pH 4.5, and 50% of this activity was inhibited by 0.31 microM esterastin. During a 48 h incubation with esterastin, the esterified cholesterol content of the cells increased to about 13 times that of control cells in the presence of low density lipoprotein and to 7 times that of control cells in the presence of cholesterol oleate liquid crystals. The ratio of esterified to free cholesterol also increased to about 5 times the control value in both conditions.
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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 ╳
