N-α-Carbobenzoxy-L-aspartic acid α-ethyl ester
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N-α-Carbobenzoxy-L-aspartic acid α-ethyl ester

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Category
CBZ-Amino Acids
Catalog number
BAT-005986
CAS number
4668-43-3
Molecular Formula
C14H17NO6
Molecular Weight
295.29
N-α-Carbobenzoxy-L-aspartic acid α-ethyl ester
IUPAC Name
(3S)-4-ethoxy-4-oxo-3-(phenylmethoxycarbonylamino)butanoate
Synonyms
Z-Asp-OEt
InChI
InChI=1S/C14H17NO6/c1-2-20-13(18)11(8-12(16)17)15-14(19)21-9-10-6-4-3-5-7-10/h3-7,11H,2,8-9H2,1H3,(H,15,19)(H,16,17)/p-1/t11-/m0/s1
InChI Key
UGURRJNSRKHEDN-NSHDSACASA-M
Canonical SMILES
CCOC(=O)C(CC(=O)[O-])NC(=O)OCC1=CC=CC=C1
1. Biocatalytic Resolution of Rac-α-Ethyl-2-Oxo-Pyrrolidineacetic Acid Methyl Ester by Immobilized Recombinant Bacillus cereus Esterase
Jian-Yong Zheng, Yin-Yan Liu, Wei-Feng Luo, Ren-Chao Zheng, Xiang-Xian Ying, Zhao Wang Appl Biochem Biotechnol. 2016 Apr;178(8):1471-80. doi: 10.1007/s12010-015-1960-0. Epub 2015 Dec 22.
A new esterase-producing strain (Bacillus cereus WZZ001) which exhibiting high hydrolytic activity and excellent enantioselectivity on rac-α-ethyl-2-oxo-pyrrolidineacetic acid methyl ester (R, S-1) has been isolated from soil sample by our laboratory. In this study, the stereoselective hydrolysis of (R, S-1) was performed using the recombinant Bacillus cereus esterase which expressed in Escherichia coli BL21 (DE3). Under the optimized conditions of pH 8.0, 35 °C, and concentration of substrate 400 mM, a successful enzymatic resolution was achieved with an e.e. s of 99.5 % and conversion of 49 %. Immobilization considerably increased the reusability of the recombinant esterase; the immobilized enzyme showed excellent reusability during 6 cycles of repeated 2 h reactions at 35 °C. Thereby, it makes the recombinant B. cereus esterase a usable biocatalyst for industrial application.
2. Prevention and reversal of obesity and glucose intolerance in mice by DHA derivatives
Martin Rossmeisl, et al. Obesity (Silver Spring). 2009 May;17(5):1023-31. doi: 10.1038/oby.2008.602. Epub 2009 Jan 15.
The n-3 polyunsaturated fatty acids, especially eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), exert hypolipidemic effects and prevent development of obesity and insulin resistance in animals fed high-fat diets. We sought to determine the efficacy of alpha-substituted DHA derivatives as lipid-lowering, antiobesity, and antidiabetic agents. C57BL/6 mice were given a corn oil-based high-fat (35% weight/weight) diet (cHF), or cHF with 1.5% of lipids replaced with alpha-methyl DHA ethyl ester (Substance 1), alpha-ethyl DHA ethyl ester (Substance 2), alpha,alpha-di-methyl DHA ethyl ester (Substance 3), or alpha-thioethyl DHA ethyl ester (Substance 4) for 4 months. Plasma markers of glucose and lipid metabolism, glucose tolerance, morphology, tissue lipid content, and gene regulation were characterized. The cHF induced obesity, hyperlipidemia, impairment of glucose homeostasis, and adipose tissue inflammation. Except for Substance 3, all other substances prevented weight gain and Substance 2 exerted the strongest effect (63% of cHF-controls). Glucose intolerance was significantly prevented (~67% of cHF) by both Substance 1 and Substance 2. Moreover, Substance 2 lowered fasting glycemia, plasma insulin, triacylglycerols, and nonesterified fatty acids (73, 9, 47, and 81% of cHF-controls, respectively). Substance 2 reduced accumulation of lipids in liver and skeletal muscle, as well as adipose tissue inflammation associated with obesity. Substance 2 also induced weight loss in dietary obese mice. In contrast to DHA administered either alone or as a component of the EPA/DHA concentrate (replacing 15% of dietary lipids), Substance 2 also reversed established glucose intolerance in obese mice. Thus, Substance 2 represents a novel compound with a promising potential in the treatment of obesity and associated metabolic disturbances.
3. Endocrine-disrupting agents on healthy human tissues
G Paganetto, F Campi, K Varani, A Piffanelli, G Giovannini, P A Borea Pharmacol Toxicol. 2000 Jan;86(1):24-9. doi: 10.1034/j.1600-0773.2000.pto860105.x.
A vast number of substances have been suggested as possibly contributing to perturbation of the endocrine system. Several have been tested with different approaches ranging from yeast expression system of human oestrogenic receptors to human breast cancer cells assays. Surprisingly, no inhibition-binding experiments to steroid receptors on healthy human tissue have been performed so far. Our study provides inhibition binding experiments to oestrogens, progesterone, testosterone and retinoic acid receptors in prostate and uterine human tissue of organochlorine pesticides, phthalate esters, oestrogenic constituents derived from plants and phenol derivates. Affinities of significant extent of phthalates on oestrogenic, progestinic and androgenic receptors have not been detected. As for retinoic acid receptors, mono(2-ethylexyl)phthalate provokes a notable reduction of the binding of the tritiated retinoic acid, phtalic acid ethyl-n-butyl ester and 4-octylphenol show an affinity comparable to that of isoflavonoid genistein, whereas 4-nonylphenol reduces the binding of retinoic acid in prostate.
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