Investigation of new potent KDO-8-phosphate synthetase inhibitors
作者： Ph. Coutrot , S. Dumarçay , Ch. Finance , M. Tabyaoui , B. Tabyaoui
DOI: 10.1016/S0960-894X(99)00111-0
关键词: Antibacterial agent 、 Aldonic acid 、 Biological activity 、 Enzyme inhibitor 、 Enzyme 、 Gram-negative bacteria 、 Organic chemistry 、 Stereochemistry 、 Chemical synthesis 、 Total synthesis 、 Chemistry
摘要: Abstract A total synthesis of ( Z , E )-D-Glucophosphoenolpyruvate and its carboxylic ester derivatives is described in four or five steps from 2,3:5,6-Di- O -isopropylidene-4- - t -butyldimethylsilyl-D-glucose
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sci-hub.se 参考文章(15)
D.H. Levin, E. Racker, Condensation of arabinose 5-phosphate and phosphorylenol pyruvate by 2-keto-3-deoxy-8-phosphooctonic acid synthetase. Journal of Biological Chemistry. ,vol. 234, pp. 2532- 2539 ,(1959) , 10.1016/S0021-9258(18)69733-9
Timor BAASOV, Shani SHEFFER-DEE-NOOR, Amnon KOHEN, Abla JAKOB, Valery BELAKHOV, Catalytic mechanism of 3-deoxy-D-manno-2-octulosonate-8-phosphate synthase. The use of synthetic analogues to probe the structure of the putative reaction intermediate. FEBS Journal. ,vol. 217, pp. 991- 999 ,(1993) , 10.1111/J.1432-1033.1993.TB18330.X
Frank M. Unger, The Chemistry and Biological Significance of 3-Deoxy-d-manno-2-Octulosonic Acid (KDO) Advances in Carbohydrate Chemistry and Biochemistry Volume 38. ,vol. 38, pp. 323- 388 ,(1981) , 10.1016/S0065-2318(08)60313-3
Garry D. Dotson, Rajesh K. Dua, James C. Clemens, E. Wrenn Wooten, Ronald W. Woodard, Overproduction and one-step purification of Escherichia coli 3-deoxy-D-manno-octulosonic acid 8-phosphate synthase and oxygen transfer studies during catalysis using isotopic-shifted heteronuclear NMR. Journal of Biological Chemistry. ,vol. 270, pp. 13698- 13705 ,(1995) , 10.1074/JBC.270.23.13698
Ph. Coutrot, C. Grison, M. Tabyaoui, A new synthesis of 3-deoxy-d-manno-2-octulosonic acid (KDO) Tetrahedron Letters. ,vol. 34, pp. 5089- 5092 ,(1993) , 10.1016/S0040-4039(00)60683-4
Tony K.M. Shing, Simple syntheses of 3,4-dideoxy-oct-2-ulosonic acids Tetrahedron Letters. ,vol. 33, pp. 1307- 1308 ,(1992) , 10.1016/S0040-4039(00)91608-3
Amnon KOHEN, Abla JAKOB, Timor BAASOV, Mechanistic studies of 3-deoxy-D-manno-2-octulosonate-8-phosphate synthase from Escherichia coli. FEBS Journal. ,vol. 208, pp. 443- 449 ,(1992) , 10.1111/J.1432-1033.1992.TB17206.X
Lizbeth Hedstrom, Robert Abeles, 3-Deoxy-D-manno-octulosonate-8-phosphate synthase catalyzes the C-O bond cleavage of phosphoenolpyruvate. Biochemical and Biophysical Research Communications. ,vol. 157, pp. 816- 820 ,(1988) , 10.1016/S0006-291X(88)80322-X
Irving J. Borowitz, Steven Firstenberg, Grace B. Borowitz, David Schuessler, Organophosphorus chemistry. XVII. Kinetics and mechanism of the Perkow reaction Journal of the American Chemical Society. ,vol. 94, pp. 1623- 1628 ,(1972) , 10.1021/JA00760A032
Takeshi Sugai, Gwo Jenn Shen, Yoshitaka Ichikawa, Chi Huey Wong, Synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO) and its analogs based on KDO aldolase-catalyzed reactions Journal of the American Chemical Society. ,vol. 115, pp. 413- 421 ,(1993) , 10.1021/JA00055A008