- Organocatalytic synthesis of optically active aryllactic acid derivatives from β-ketosulfoxides
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The organocatalytic synthesis of new α-acyloxy-3-arylpropionic thioesters has been accomplished providing some enantioenriched important aryllactic acid derivatives in good yield and enantioselectivities.
- Capitta, Francesca,Melis, Nicola,Secci, Francesco,Romanazzi, Giuseppe,Frongia, Angelo
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p. 649 - 660
(2015/10/19)
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- Inhibition of the severe acute respiratory syndrome 3CL protease by peptidomimetic α,β-unsaturated esters
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The proteolytic processing of polyproteins by the 3CL protease of severe acute respiratory syndrome coronavirus is essential for the viral propagation. A series of tripeptide α,β-unsaturated esters and ketomethylene isosteres, including AG7088, are synthesized and assayed to target the 3CL protease. Though AG7088 is inactive (IC50 > 100 μM), the ketomethylene isosteres and tripeptide α,β-unsaturated esters containing both P1 and P2 phenylalanine residues show modest inhibitory activity (IC50 = 11-39 μM). The Phe-Phe dipeptide inhibitors 18a-e are designed on the basis of computer modeling of the enzyme-inhibitor complex. The most potent inhibitor 18c with an inhibition constant of 0.52 μM is obtained by condensation of the Phe-Phe dipeptide α,β-unsaturated ester with 4-(dimethylamino)cinnamic acid. The cell-based assays also indicate that 18c is a nontoxic anti-SARS agent with an EC50 value of 0.18 μM.
- Shie, Jiun-Jie,Fang, Jim-Min,Kuo, Tun-Hsun,Kuo, Chih-Jung,Liang, Po-Huang,Huang, Hung-Jyun,Wu, Yin-Ta,Jan, Jia-Tsrong,Cheng, Yih-Shyun E.,Wong, Chi-Huey
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p. 5240 - 5252
(2007/10/03)
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- Development of a continuous enzymatic process for the preparation of (R)-3-(4-fluorophenyl)-2-hydroxy propionic acid
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While many methods have been reported for the synthesis of chiral 2-hydroxy acids, few of them have proven to be reliable toward the synthesis of the title compound in terms of overall yield and enantioselectivity. Herein we describe a continuous enzymatic process for an efficient synthesis of (R)-3-(4-fluorophenyl)-2-hydroxy propionic acid at multikilogram scale with a high space-time yield (560 g/(L·d)) using a membrane reactor. The product was generated in excellent enantiomeric excess (ee > 99.9%) and good overall yield (68-72%).
- Tao, Junhua,McGee, Kevin
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p. 520 - 524
(2013/09/06)
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