Portal de Periódicos da CAPES

Racemase Activity of B. cepacia Lipase Leads to Dual‐Function Asymmetric Dynamic Kinetic Resolution of α‐Aminonitriles

2011; Wiley; Volume: 50; Issue: 29 Linguagem: Inglês

10.1002/anie.201007373

1521-3773

Pornrapee Vongvilai, Mats Linder, Morakot Sakulsombat, Maria Svedendahl Humble, Per Berglund, Tore Brinck, Olof Ramström,

Protein Structure and Dynamics

Angewandte Chemie International EditionVolume 50, Issue 29 p. 6592-6595 Communication Racemase Activity of B. cepacia Lipase Leads to Dual-Function Asymmetric Dynamic Kinetic Resolution of α-Aminonitriles† Dr. Pornrapee Vongvilai, Dr. Pornrapee Vongvilai Department of Chemistry, KTH—Royal Institute of Technology, Teknikringen 30, 10044 Stockholm (Sweden), Fax: (+46) 8-791-2333Search for more papers by this authorMats Linder, Mats Linder Department of Chemistry, KTH—Royal Institute of Technology, Teknikringen 30, 10044 Stockholm (Sweden), Fax: (+46) 8-791-2333 These authors contributed equally.Search for more papers by this authorMorakot Sakulsombat, Morakot Sakulsombat Department of Chemistry, KTH—Royal Institute of Technology, Teknikringen 30, 10044 Stockholm (Sweden), Fax: (+46) 8-791-2333 These authors contributed equally.Search for more papers by this authorDr. Maria Svedendahl Humble, Dr. Maria Svedendahl Humble School of Biotechnology, KTH—Royal Institute of Technology, AlbaNova University Center, 106 91 Stockholm (Sweden)Search for more papers by this authorProf. Per Berglund, Prof. Per Berglund School of Biotechnology, KTH—Royal Institute of Technology, AlbaNova University Center, 106 91 Stockholm (Sweden)Search for more papers by this authorProf. Tore Brinck, Prof. Tore Brinck Department of Chemistry, KTH—Royal Institute of Technology, Teknikringen 30, 10044 Stockholm (Sweden), Fax: (+46) 8-791-2333Search for more papers by this authorProf. Olof Ramström, Corresponding Author Prof. Olof Ramström [email protected] Department of Chemistry, KTH—Royal Institute of Technology, Teknikringen 30, 10044 Stockholm (Sweden), Fax: (+46) 8-791-2333Department of Chemistry, KTH—Royal Institute of Technology, Teknikringen 30, 10044 Stockholm (Sweden), Fax: (+46) 8-791-2333Search for more papers by this author Dr. Pornrapee Vongvilai, Dr. Pornrapee Vongvilai Department of Chemistry, KTH—Royal Institute of Technology, Teknikringen 30, 10044 Stockholm (Sweden), Fax: (+46) 8-791-2333Search for more papers by this authorMats Linder, Mats Linder Department of Chemistry, KTH—Royal Institute of Technology, Teknikringen 30, 10044 Stockholm (Sweden), Fax: (+46) 8-791-2333 These authors contributed equally.Search for more papers by this authorMorakot Sakulsombat, Morakot Sakulsombat Department of Chemistry, KTH—Royal Institute of Technology, Teknikringen 30, 10044 Stockholm (Sweden), Fax: (+46) 8-791-2333 These authors contributed equally.Search for more papers by this authorDr. Maria Svedendahl Humble, Dr. Maria Svedendahl Humble School of Biotechnology, KTH—Royal Institute of Technology, AlbaNova University Center, 106 91 Stockholm (Sweden)Search for more papers by this authorProf. Per Berglund, Prof. Per Berglund School of Biotechnology, KTH—Royal Institute of Technology, AlbaNova University Center, 106 91 Stockholm (Sweden)Search for more papers by this authorProf. Tore Brinck, Prof. Tore Brinck Department of Chemistry, KTH—Royal Institute of Technology, Teknikringen 30, 10044 Stockholm (Sweden), Fax: (+46) 8-791-2333Search for more papers by this authorProf. Olof Ramström, Corresponding Author Prof. Olof Ramström [email protected] Department of Chemistry, KTH—Royal Institute of Technology, Teknikringen 30, 10044 Stockholm (Sweden), Fax: (+46) 8-791-2333Department of Chemistry, KTH—Royal Institute of Technology, Teknikringen 30, 10044 Stockholm (Sweden), Fax: (+46) 8-791-2333Search for more papers by this author First published: 01 June 2011 https://doi.org/10.1002/anie.201007373Citations: 35 † This study was supported by the Swedish Research Council and the Royal Institute of Technology. We thank Toyo Denka Kogyo Co. and Dr. Y. Yamashita for providing samples for this study. Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Applaudable promiscuity: Racemase-type activity discovered for B. cepacia lipase with N-substituted α-aminonitriles is proposed to involve a CC bond-breaking/forming mechanism in the hydrolase site of the enzyme, as supported by experimental data and calculations. This promiscuous activity in combination with the transacylation activity of the enzyme enabled the asymmetric synthesis of N-methyl α-aminonitrile amides in high yield (see scheme). Supporting Information Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description anie_201007373_sm_miscellaneous_information.pdf1.1 MB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. References 1R. Noyori, Nat. Chem. 2009, 1, 5–6. 2M. Breuer, K. Ditrich, T. Habicher, B. Hauer, M. Keßeler, R. Stürmer, T. Zelinski, Angew. Chem. 2004, 116, 806–843; Angew. Chem. Int. Ed. 2004, 43, 788–824. 3A. Ghanem, Tetrahedron 2007, 63, 1721–1754. 4H. E. Schoemaker, D. Mink, M. G. Wubbolts, Science 2003, 299, 1694–1697. 5For recent accounts, see: 5aD. Liu, P. Trodler, S. Eiben, K. Koschorreck, M. Müller, J. Pleiss, S. C. Maurer, C. Branneby, R. D. Schmid, B. Hauer, ChemBioChem 2010, 11, 789–795; 5bN. Ríos-Lombardía, E. Busto, V. Gotor-Fernández, V. Gotor, R. Porcar, E. García-Verdugo, S. V. Luis, I. Alfonso, S. García-Granda, A. Menéndez-Velázquez, Chem. Eur. J. 2010, 16, 836–847; 5cM. Vallin, P.-O. Syrén, K. Hult, ChemBioChem 2010, 11, 411–416; 5dT. Ema, S. Kamata, M. Takeda, Y. Nakano, T. Sakai, Chem. Commun. 2010, 46, 5440–5442; 5eS. Akai, R. Hanada, N. Fujiwara, Y. Kita, M. Egi, Org. Lett. 2010, 12, 4900–4903; 5fL. H. Andrade, T. Barcellos, Org. Lett. 2009, 11, 3052–3055; 5gR. O. de Souza, O. A. C. Antunes, W. Kroutil, C. O. Kappe, J. Org. Chem. 2009, 74, 6157–6162; 5hP. Vongvilai, R. Larsson, O. Ramström, Adv. Synth. Catal. 2008, 350, 448–452; 5iM.-J. Kim, Y. K. Choi, S. Kim, D. Kim, K. Han, S.-B. Ko, J. Park, Org. Lett. 2008, 10, 1295–1298; 5jP. Vongvilai, M. Angelin, R. Larsson, O. Ramström, Angew. Chem. 2007, 119, 966–968; Angew. Chem. Int. Ed. 2007, 46, 948–950; 5kN. M. T. Lourenço, C. A. M. Afonso, Angew. Chem. 2007, 119, 8326; Angew. Chem. Int. Ed. 2007, 46, 8178–8181; 5lY. Zhu, K.-L. Fow, G.-K. Chuah, S. Jaenicke, Chem. Eur. J. 2007, 13, 541–547; 5mB. A. C. van As, J. van Buijtenen, T. Mes, A. R. A. Palmans, E. W. Meijer, Chem. Eur. J. 2007, 13, 8325–8332. 6M. Rodríguez-Mata, E. García-Urdiales, V. Gotor-Fernández, V. Gotor, Adv. Synth. Catal. 2010, 352, 395–406. 7M. Shakeri, K. Engström, A. G. Sandström, J.-E. Bäckvall, ChemCatChem 2010, 2, 534–538. 8L. K. Thalén, D. Zhao, J.-B. Sortais, J. Paetzold, C. Hoben, J.-E. Bäckvall, Chem. Eur. J. 2009, 15, 3403–3410. 9V. Gotor-Fernández, E. Busto, V. Gotor, Adv. Synth. Catal. 2006, 348, 797–812. 10F. van Rantwijk, R. A. Sheldon, Tetrahedron 2004, 60, 501–519. 11G. Asensio, C. Andreu, J. A. Marco, Tetrahedron Lett. 1991, 32, 4197–4198. 12T.-W. Chiou, C.-C. Chang, C.-T. Lai, D.-F. Tai, Bioorg. Med. Chem. Lett. 1997, 7, 433–436. 13G. F. Breen, Tetrahedron: Asymmetry 2004, 15, 1427–1430. 14V. Gotor-Fernández, P. Fernández-Torres, V. Gotor, Tetrahedron: Asymmetry 2006, 17, 2558–2564. 15A. J. Blacker, M. J. Stirling, M. I. Page, Org. Process Res. Dev. 2007, 11, 642–648. 16A. Liljeblad, H.-M. Kavenius, P. Taehtinen, L. T. Kanerva, Tetrahedron: Asymmetry 2007, 18, 181–191. 17P. Vongvilai, O. Ramström, J. Am. Chem. Soc. 2009, 131, 14419–14425. 18H. Gröger, Chem. Rev. 2003, 103, 2795–2827. 19K. Nakai, J. Hiratake, J. i. Oda, Bull. Inst. Chem. Res. 1992, 70, 333–337. 20P. López-Serrano, J. A. Jongejan, F. van Rantwijk, R. A. Sheldon, Tetrahedron: Asymmetry 2001, 12, 219–228. 21Racemization effects were observed for cyanoalkyl acetamides when preparations of Candida antarctica lipase B were used in the presence of a zeolite.[20] 22U. T. Bornscheuer, R. J. Kazlauskas, Angew. Chem. 2004, 116, 6156–6165; Angew. Chem. Int. Ed. 2004, 43, 6032–6040. 23A. Aharoni, L. Gaidukov, O. Khersonsky, S. M. Gould, C. Roodveldt, D. S. Tawfik, Nat. Genet. 2005, 37, 73–76. 24K. Hult, P. Berglund, Trends Biotechnol. 2007, 25, 231–238. 25H. Pellissier, Tetrahedron 2008, 64, 1563–1601. 26A. H. Kamaruddin, M. H. Uzir, H. Y. Aboul-Enein, H. N. A. Halim, Chirality 2009, 21, 449–467. 27B. Martín-Matute, J.-E. Bäckvall, Curr. Opin. Chem. Biol. 2007, 11, 226–232. 28See the Supporting Information for more details. 29 29aP. Carlqvist, M. Svedendahl, C. Branneby, K. Hult, T. Brinck, P. Berglund, ChemBioChem 2005, 6, 331–336; 29bC. Branneby, P. Carlqvist, A. Magnusson, K. Hult, T. Brinck, P. Berglund, J. Am. Chem. Soc. 2003, 125, 874–875; 29cM. Persson, E. Wehtje, P. Adlercreutz, ChemBioChem 2002, 3, 566–571; 29dC. Bovet, R. Zenobi, Anal. Biochem. 2008, 373, 380–382; 29eD. Rotticci, T. Norin, K. Hult, M. Martinelle, Biochim. Biophys. Acta Mol. Cell Biol. Lipids 2000, 1483, 132–140. Citing Literature Volume50, Issue29July 11, 2011Pages 6592-6595 ReferencesRelatedInformation