Computational design of enone-binding proteins with catalytic activity for the morita-baylis-hillman reaction
作者： Sinisa Bjelic , Lucas G Nivón , Nihan Çelebi-Ölçüm , Gert Kiss , Carolyn F Rosewall
DOI: 10.1021/CB3006227
关键词: Michael reaction 、 Active site 、 Reaction mechanism 、 Nucleophile 、 Baylis–Hillman reaction 、 Catalysis 、 Electrophile 、 Enone 、 Chemistry 、 Stereochemistry
摘要: … Morita–Baylis–Hillman reaction: how do optimal enzyme active sites compare with organocatalysts. Catalysis Science & Technology 2022, 20 https://doi.org/10.1039/D2CY00929C …
acs.org
sci-hub.se 参考文章(25)
Florian Richter, Andrew Leaver-Fay, Sagar D. Khare, Sinisa Bjelic, David Baker, De novo enzyme design using Rosetta3. PLOS ONE. ,vol. 6, ,(2011) , 10.1371/JOURNAL.PONE.0019230
Leleti Rajender Reddy, P. Saravanan, E. J. Corey, Simple stereocontrolled synthesis of salinosporamide a Journal of the American Chemical Society. ,vol. 126, pp. 6230- 6231 ,(2005) , 10.1021/JA048613P
Manfred T. Reetz, Régis Mondière, José Daniel Carballeira, Enzyme promiscuity: first protein-catalyzed Morita-Baylis-Hillman reaction Tetrahedron Letters. ,vol. 48, pp. 1679- 1681 ,(2007) , 10.1016/J.TETLET.2007.01.063
Raphaël Robiette, Varinder K Aggarwal, Jeremy N. Harvey, Mechanism of the Morita-Baylis-Hillman reaction: A computational investigation Journal of the American Chemical Society. ,vol. 129, pp. 15513- 15525 ,(2007) , 10.1021/JA0717865
Alpay Dermenci, Philipp S. Selig, Robert A. Domaoal, Krasimir A. Spasov, Karen S. Anderson, Scott J. Miller, Quasi-Biomimetic Ring Contraction Catalyzed by a Cysteine-Based Nucleophile: Total Synthesis of Sch-642305, Some Analogs and their Putative anti-HIV Activities. Chemical Science. ,vol. 2, pp. 1568- 1572 ,(2011) , 10.1039/C1SC00221J
J. B. Siegel, A. Zanghellini, H. M. Lovick, G. Kiss, A. R. Lambert, J. L. St.Clair, J. L. Gallaher, D. Hilvert, M. H. Gelb, B. L. Stoddard, K. N. Houk, F. E. Michael, D. Baker, Computational design of an enzyme catalyst for a stereoselective bimolecular Diels-Alder reaction Science. ,vol. 329, pp. 309- 313 ,(2010) , 10.1126/SCIENCE.1190239
Ken-ichi Morita, Zennosuke Suzuki, Hiromitsu Hirose, A Tertiary Phosphine-catalyzed Reaction of Acrylic Compounds with Aldehydes Bulletin of the Chemical Society of Japan. ,vol. 41, pp. 2815- 2815 ,(1968) , 10.1246/BCSJ.41.2815
Florian Richter, Rebecca Blomberg, Sagar D. Khare, Gert Kiss, Alexandre P. Kuzin, Adam J. T. Smith, Jasmine Gallaher, Zbigniew Pianowski, Roger C. Helgeson, Alexej Grjasnow, Rong Xiao, Jayaraman Seetharaman, Min Su, Sergey Vorobiev, Scott Lew, Farhad Forouhar, Gregory J. Kornhaber, John F. Hunt, Gaetano T. Montelione, Liang Tong, K. N. Houk, Donald Hilvert, David Baker, Computational design of catalytic dyads and oxyanion holes for ester hydrolysis. Journal of the American Chemical Society. ,vol. 134, pp. 16197- 16206 ,(2012) , 10.1021/JA3037367
L. Jiang, E. A. Althoff, F. R. Clemente, L. Doyle, D. Rothlisberger, A. Zanghellini, J. L. Gallaher, J. L. Betker, F. Tanaka, C. F. Barbas, D. Hilvert, K. N. Houk, B. L. Stoddard, D. Baker, De novo computational design of retro-aldol enzymes. Science. ,vol. 319, pp. 1387- 1391 ,(2008) , 10.1126/SCIENCE.1152692
Varinder K. Aggarwal, David K. Dean, Andrea Mereu, Richard Williams, Rate acceleration of the Baylis-Hillman reaction in polar solvents (water and formamide). Dominant role of hydrogen bonding, not hydrophobic effects, is implicated. Journal of Organic Chemistry. ,vol. 67, pp. 510- 514 ,(2002) , 10.1021/JO016073Y