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M.","year":"1995","journal-title":"Cancer Res."},{"key":"ref2\/cit2","doi-asserted-by":"crossref","first-page":"1567","DOI":"10.1002\/anie.199615671","volume":"35","author":"Hofle G. H.","year":"1996","journal-title":"Angew. Chem., Int. Ed. Engl."},{"key":"ref3\/cit3","first-page":"2015","volume":"37","author":"Nicolaou K. C.","year":"1998","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref4\/cit4","doi-asserted-by":"crossref","first-page":"1336","DOI":"10.1016\/j.crci.2008.02.005","volume":"11","author":"Mulzer J.","year":"2008","journal-title":"C. R. Chim."},{"key":"ref5\/cit5","first-page":"1","volume":"9","author":"Reichenbach H.","year":"2008","journal-title":"Drugs Res. Dev."},{"key":"ref6\/cit6","doi-asserted-by":"crossref","first-page":"2015","DOI":"10.1200\/JCO.2004.12.001","volume":"22","author":"Goodin S.","year":"2004","journal-title":"J. Clin. Oncol."},{"key":"ref7\/cit7","doi-asserted-by":"crossref","first-page":"2801","DOI":"10.1002\/anie.199628011","volume":"35","author":"Balog A.","year":"1996","journal-title":"Angew. Chem., Int. Ed. Engl."},{"key":"ref8\/cit8","doi-asserted-by":"crossref","first-page":"2399","DOI":"10.1002\/anie.199623991","volume":"35","author":"Nicolaou K. C.","year":"1996","journal-title":"Angew. Chem., Int. Ed. Engl."},{"key":"ref9\/cit9","doi-asserted-by":"crossref","first-page":"757","DOI":"10.1002\/anie.199707571","volume":"36","author":"Su D. S.","year":"1997","journal-title":"Angew. Chem., Int. Ed. Engl."},{"key":"ref10\/cit10","doi-asserted-by":"crossref","first-page":"2675","DOI":"10.1002\/(SICI)1521-3773(19981016)37:19<2675::AID-ANIE2675>3.0.CO;2-O","volume":"37","author":"Balog A.","year":"1998","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref11\/cit11","doi-asserted-by":"crossref","first-page":"3031","DOI":"10.1016\/S0960-894X(98)00546-0","volume":"8","author":"Sefkow M.","year":"1998","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref12\/cit12","doi-asserted-by":"crossref","first-page":"2693","DOI":"10.1021\/ol016273w","volume":"3","author":"Regueiro-Ren A.","year":"2001","journal-title":"Org. Lett."},{"key":"ref13\/cit13","doi-asserted-by":"crossref","first-page":"3815","DOI":"10.1021\/ol026589j","volume":"4","author":"Regueiro-Ren A.","year":"2002","journal-title":"Org. Lett."},{"key":"ref14\/cit14","doi-asserted-by":"crossref","first-page":"3515","DOI":"10.1002\/anie.200351819","volume":"42","author":"Nicolaou K. C.","year":"2003","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref15\/cit15","doi-asserted-by":"crossref","first-page":"3186","DOI":"10.1021\/ol900971r","volume":"11","author":"Frein J. D.","year":"2009","journal-title":"Org. Lett."},{"key":"ref16\/cit16","doi-asserted-by":"crossref","first-page":"4529","DOI":"10.1016\/S0040-4039(97)00931-3","volume":"38","author":"Balog A.","year":"1997","journal-title":"Tetrahedron Lett."},{"key":"ref17\/cit17","doi-asserted-by":"crossref","first-page":"41","DOI":"10.1002\/cmdc.200500056","volume":"1","author":"Nicolaou K. C.","year":"2006","journal-title":"ChemMedChem"},{"key":"ref18\/cit18","doi-asserted-by":"crossref","first-page":"7224","DOI":"10.1021\/jo991014u","volume":"64","author":"Taylor R. E.","year":"1999","journal-title":"J. Org. Chem."},{"key":"ref19\/cit19","doi-asserted-by":"crossref","first-page":"26","DOI":"10.1021\/ja028196l","volume":"125","author":"Taylor R. E.","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"ref20\/cit20","doi-asserted-by":"crossref","first-page":"43","DOI":"10.1021\/ol990521v","volume":"1","author":"Wang M. M.","year":"1999","journal-title":"Org. Lett."},{"key":"ref21\/cit21","doi-asserted-by":"crossref","first-page":"44886","DOI":"10.1074\/jbc.M308115200","volume":"278","author":"Nagano S.","year":"2003","journal-title":"J. Biol. Chem."},{"key":"ref22\/cit22","first-page":"209","volume-title":"Tubulin-Binding Agents: Synthetic, Structural and Mechanistic Insights","author":"Nettles J. H.","year":"2009"},{"key":"ref23\/cit23","doi-asserted-by":"crossref","first-page":"866","DOI":"10.1126\/science.1099190","volume":"305","author":"Nettles J. H.","year":"2004","journal-title":"Science"},{"key":"ref24\/cit24","doi-asserted-by":"crossref","first-page":"2511","DOI":"10.1002\/anie.200351276","volume":"42","author":"Carlomagno T.","year":"2003","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref25\/cit25","doi-asserted-by":"crossref","first-page":"1469","DOI":"10.1021\/jm7013452","volume":"51","author":"Erdelyi M.","year":"2008","journal-title":"J. Med. Chem."},{"key":"ref26\/cit26","doi-asserted-by":"crossref","first-page":"1864","DOI":"10.1002\/anie.200604505","volume":"46","author":"Reese M.","year":"2007","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref27\/cit27","doi-asserted-by":"crossref","first-page":"3097","DOI":"10.1021\/jp983679q","volume":"103","author":"Ballone P.","year":"1999","journal-title":"J. Phys. Chem. A"},{"key":"ref28\/cit28","doi-asserted-by":"crossref","first-page":"967","DOI":"10.1002\/qua.21566","volume":"108","author":"Kamel K.","year":"2008","journal-title":"Int. J. Quantum Chem."},{"key":"ref29\/cit29","doi-asserted-by":"crossref","first-page":"859","DOI":"10.1007\/s00894-008-0428-3","volume":"15","author":"Rusinska-Roszak D.","year":"2009","journal-title":"J. Mol. Model."},{"key":"ref30\/cit30","doi-asserted-by":"crossref","first-page":"209","DOI":"10.1002\/jcc.540100208","volume":"10","author":"Stewart J. J. P.","year":"1989","journal-title":"J. Comput. Chem."},{"key":"ref31\/cit31","doi-asserted-by":"crossref","first-page":"221","DOI":"10.1002\/jcc.540100209","volume":"10","author":"Stewart J. J. P.","year":"1989","journal-title":"J. Comput. Chem."},{"key":"ref32\/cit32","doi-asserted-by":"crossref","first-page":"10518","DOI":"10.1021\/jp047502+","volume":"108","author":"Su J. T.","year":"2004","journal-title":"J. Phys. Chem. A"},{"key":"ref33\/cit33","doi-asserted-by":"crossref","first-page":"2673","DOI":"10.1073\/pnas.0308730100","volume":"101","author":"Xu X.","year":"2004","journal-title":"Proc. Natl. Acad. Sci. U.S.A."},{"key":"ref34\/cit34","first-page":"1","volume":"122","author":"Xu X.","year":"2005","journal-title":"J. Chem. Phys."},{"key":"ref35\/cit35","unstructured":"Preliminary calculations revealed that increasing the size of the basis set does not induce any quantitative change in the optimized geometry of epothilone A. Optimized geometries and RMSD heavy-atom differences for tested epothilone conformers can be requested from the author. The B3LYP\/6-311++G(d,p) method was employed to refine the energy calculation on structures that were probed to be unaltered as compared to B3LYP\/6-31G(d). The use of single point calculations at B3LYP\/6-311++G(d,p) is significantly cheaper in computational cost than optimization procedures at this level of theory, especially for the case of large systems as epothilones."},{"key":"ref36\/cit36","unstructured":"Frisch, M. J.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Wong, M. W.; Gonzalez, C.; Pople, J. A.Gaussian 03;Gaussian, Inc.:Wallingford, CT, 2004."},{"key":"ref37\/cit37","doi-asserted-by":"crossref","first-page":"41","DOI":"10.1023\/A:1011140723828","volume":"15","author":"Lee K. W.","year":"2001","journal-title":"J. Comput.-Aided Mol. Des."},{"key":"ref38\/cit38","doi-asserted-by":"crossref","first-page":"453","DOI":"10.1002\/cjoc.200790086","volume":"25","author":"Yuan W.","year":"2007","journal-title":"Chin. J. Chem."},{"key":"ref39\/cit39","doi-asserted-by":"crossref","first-page":"1781","DOI":"10.1002\/jcc.20289","volume":"26","author":"Phillips J. C.","year":"2005","journal-title":"J. Comput. Chem."},{"key":"ref40\/cit40","doi-asserted-by":"crossref","first-page":"86","DOI":"10.1002\/(SICI)1096-987X(20000130)21:2<86::AID-JCC2>3.0.CO;2-G","volume":"21","author":"Foloppe N.","year":"2000","journal-title":"J. Comput. Chem."},{"key":"ref41\/cit41","doi-asserted-by":"crossref","first-page":"765","DOI":"10.1002\/prot.22102","volume":"73","author":"Bas D. C.","year":"2008","journal-title":"Proteins"},{"key":"ref42\/cit42","doi-asserted-by":"crossref","first-page":"2575","DOI":"10.1002\/jcc.20999","volume":"29","author":"Kieseritzky G.","year":"2008","journal-title":"J. Comput. Chem."},{"key":"ref43\/cit43","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1007\/BF02289451","volume":"31","author":"Schoenemann P. 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