130622-05-8Relevant articles and documents
Expedient synthesis of (+)-lycopalhine A
Williams, Benjamin M.,Trauner, Dirk
, p. 2191 - 2194 (2016)
Two amino acids play a key role in the first total synthesis of lycopalhine A. l-glutamic acid serves as a convenient chiral starting material for the 13-step synthesis, and l-proline promotes an unusual 5-endo-trig Mannich cyclization that generates the central pyrrolidine ring of the Lycopodium alkaloid. The bicyclo[3.3.0]octanol moiety of the molecule is formed through an intramolecular aldol addition that may occur spontaneously in nature. Just Another Mannich Monday: By using l-glutamate and l-proline as a starting material and catalyst, respectively, the complex alkaloid lycopalhine A was assembled in only 13 steps. The synthesis features not only an unusual Mannich reaction but also a biomimetic aldol addition that completes the intricate carbon skeleton of the natural product.
Synthesis of cis -5-trifluoromethylproline from l -glutamic acid
Ortial, Stéphanie,Dave, Rajesh,Benfodda, Zohra,Bénimélis, David,Meffre, Patrick
, p. 569 - 573 (2014)
The diastereoselective synthesis of cis-5-trifluoromethylproline (5-Tfm-Pro) from l-glutamic acid is described. 5-Tfm-Pro could be obtained through a seven-step linear sequence. Trifluoromethylation of the glutamic-derived ester or aldehyde and subsequent reduction of the cyclic imine are the key steps in the synthesis. Georg Thieme Verlag Stuttgart New York.
A practical and efficient synthesis of thalidomide via Na/liquid NH 3 methodology
Varala, Ravi,Adapa, Srinivas R.
, p. 853 - 856 (2005)
A facile, efficient, concise, cost-effective, and scalable synthesis of thalidomide in high overall yield (55%) is presented. Treatment of Boc-protected L-glutamic acid diester via Na/ liquid (liq.) NH3 (-33°C) mediated cyclization methodology produces a corresponding glutarimide ring which was subsequently condensed with phthalic anhydride in the presence of glacial acetic acid to afford thalidomide.
Efficient and selective cleavage of the t-butoxycarbonyl group from di-t-butylimidodicarbonate using catalytic bismuth(III) bromide in acetonitrile
Zheng, Jianlong,Yin, Biaolin,Huang, Wenming,Li, Xiaopeng,Yao, Hequan,Liu, Zhaogui,Zhang, Jiancun,Jiang, Sheng
, p. 5094 - 5097 (2009)
Di-t-butylimidodicarbonates can be chemoselectively and efficiently deprotected to the corresponding mono-BOC-protected amines in high yields using a catalytic amount of bismuth(III) bromide in acetonitrile at room temperature. This method is mild and compatible with the presence of a wide range of functional and other protecting groups in the substrates, such as TBDMS, MOM and mono-BOC or Cbz-protected amines, etc. The method has advantages of ease of operation and use of nontoxic and inexpensive catalyst.
Preparation of a metal-ligand fluorescent chemosensor and enantioselective recognition of carboxylate anions in aqueous solution
Chen, Zhi-hong,He, Yong-bing,Hu, Chen-Guang,Huang, Xiao-huan
, p. 2051 - 2057 (2008)
Two chiral fluorescent chemosensors 1 and 2 were synthesized, and the structure characterized by IR, 1H NMR, 13C NMR, MS spectra and elemental analysis. Their recognition ability was studied in aqueous solution (Tris-HCl buffer pH 7.4, MeOH/H2O = 1:1) through fluorescence spectra. Receptors 1 and 2 showed a good binding ability to the copper ion. The host 1-Cu2+ complex showed a chiral recognition ability to mandelate anions with a preferable binding to l-mandelate than d-mandelate anions. The host 1-Cu2+ complex and l- or d-mandelate anions formed 1:1 stoichiometric complex. The binding constant for l-mandelate is 576 M-1, whereas that for d-mandelate is only 38 M-1, which can be distinguished by the different change of fluorescence intensity.
Target-guided screening of fragments (TGSOF) in the discovery of inhibitors against EV-A71 3C protease
Fu, Shengjun,Nie, Quandeng,Ma, Yuying,Song, Ping,Ren, Xuejiao,Luo, Cheng,Shang, Luqing,Yin, Zheng
, p. 2890 - 2893 (2018)
Target-guided screening of fragments (TGSOF) was developed and employed in the identification of EV-A71 3C protease (3Cpro) inhibitors. We identified 4-acetylpyridine and 3-acetylpyridine as effective P3 fragments of an inhibitor and obtained the corresponding irreversible inhibitors 12c and 12fvia this method. Furthermore, based on 12c and 12f, we have obtained reversible inhibitors 17c and 17f. These results demonstrated that TGSOF is a useful strategy for identifying suitable fragments in developing leads in drug discovery.
Cyanohydrin as an anchoring group for potent and selective inhibitors of enterovirus 71 3C protease
Zhai, Yangyang,Zhao, Xiangshuai,Cui, Zhengjie,Wang, Man,Wang, Yaxin,Li, Linfeng,Sun, Qi,Yang, Xi,Zeng, Debin,Liu, Ying,Sun, Yuna,Lou, Zhiyong,Shang, Luqing,Yin, Zheng
, p. 9414 - 9420 (2015)
Cyanohydrin derivatives as enterovirus 71 (EV71) 3C protease (3Cpro) inhibitors have been synthesized and assayed for their biochemical and antiviral activities. Compared with the reported inhibitors, cyanohydrins (1S,2S,2′S,5S)-16 and (1R,2S,2′S,5S)-16 exhibited significantly improved activity and attractive selectivity profiles against other proteases, which were a result of the specific interactions between the cyanohydrin moiety and the catalytic site of 3Cpro. Cyanohydrin as an anchoring group with high selectivity and excellent inhibitory activity represents a useful choice for cysteine protease inhibitors.
L-glutamic acid derivative and synthesis method and application thereof
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Paragraph 0044; 0048-0052; 0056; 00060-0064; 0066; 0070-0074, (2020/11/01)
The invention belongs to the technical field of synthesis of medical and traditional Chinese medicine intermediates, and discloses an L-glutamic acid derivative and a synthesis method and applicationthereof. All the steps in the synthesis method are simple and in order , the obtained L-dimethyl glutamate hydrochloride oily matter is directly put into the next step of reaction through a one-pot method, L-dimethyl glutamate hydrochloride solids do not need to be obtained, the use of all the raw materials can be effectively reduced, and the cost is reduced; ethyl acetate is selected as a reaction solvent and can be effectively recycled, the utilization rate of the ethyl acetate is remarkably increased, and pollution to the environment is reduced; a final product is obtained in a crystallization manner so that the convenience and the storage convenience during transportation are improved, and the quality and the yield of the product can be further improved. The technical scheme of the synthesis method is complete and simple, the produced product is high in crystallization yield and better in quality, the overall yield of the product is conveniently, rapidly, scientifically and effectively increased to 85% or above, and raw materials are provided for research and development of new drugs.
Synthesis and Biological Evaluation of a Library of AGE-Related Amino Acid Triazole Crosslinkers
Agelidis, Nektarios,Altevogt, Luca,Baro, Angelika,Bilitewski, Ursula,Bugdayci, Bakiye,Icik, Esra,Jolly, Anthony,L?ffler, Paul,Laschat, Sabine
supporting information, (2020/09/01)
Three N-Boc-protected amino acids, l-serine, l-aspartic, and l-glutamic acid, were either converted into their methyl azidoalkanoates or various alkynes via Bestmann-Ohira strategy or via reaction with propargylamine and propargyl bromide, respectively. The Cu-catalyzed click reaction provided a library of amino acid based triazoles, which were further N-methylated to triazolium iodides or deprotected and precipitated as free amino acid triazole dihydrochlorides. The biological properties of all derivatives were investigated by cytotoxicity assay (against L929 mouse fibroblasts) and broth microdilution method (E. coli ΔTolC and S. aureus). First results reveal complete inactivity for triazolium iodides with cell viabilities and microbial growths nearly 100 %, indicating them as possible analogs of advanced glycation endproducts (AGEs).
