Synlett, Inhaltsverzeichnis Synlett 2015; 26(04): 461-466DOI: 10.1055/s-0034-1378938 letter © Georg Thieme Verlag Stuttgart · New YorkClick To Bind: Microwave-Assisted Solid-Phase Synthesis of Peptoids Incorporating Pyridine–Triazole Ligands and Their Copper(II) Complexes Tamar Zabrodski Schulich Faculty of Chemistry, Technion – Israel Institute of Technology, Haifa, 3200008, Israel Fax: +972(4)8293947 eMail: gm92@tx.technion.ac.il , Maria Baskin Schulich Faculty of Chemistry, Technion – Israel Institute of Technology, Haifa, 3200008, Israel Fax: +972(4)8293947 eMail: gm92@tx.technion.ac.il , Prathap Jeya Kaniraj Schulich Faculty of Chemistry, Technion – Israel Institute of Technology, Haifa, 3200008, Israel Fax: +972(4)8293947 eMail: gm92@tx.technion.ac.il , Galia Maayan* Schulich Faculty of Chemistry, Technion – Israel Institute of Technology, Haifa, 3200008, Israel Fax: +972(4)8293947 eMail: gm92@tx.technion.ac.il› InstitutsangabenArtikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract We describe a fast and efficient incorporation of the ligands 2-(1H-1,2,3-triazol-4-yl)pyridine and 2-(1H-1,2,3-triazol-1-ylmethyl)-pyridine into N-substituted glycine peptoid oligomers by the azide–alkyne cycloaddition (click) reaction on a solid support under microwave irradiation. Peptoids bearing these ligands formed stable complexes with copper(II). Key words Key wordsclick reactions - cycloadditions - triazoles - solid-phase synthesis - peptides Volltext Referenzen References 1 Seo J, Lee BC, Zuckermann RN In Comprehensive Biomaterials: Ducheyne P. Vol. 2. Chap. 2.204 Elsevier; Amsterdam: 2011: 53 2a Kirshenbaum K, Barron AE, Goldsmith RA, Armand P, Bradley E, Truong KT. V, Dill KA, Cohen FE, Zuckermann RN. Proc. Natl. Acad. Sci. U.S.A. 1998; 95: 4303 2b Wu CW, Sanborn TJ, Zuckermann RN, Barron AE. J. Am. Chem. Soc. 2001; 123: 2958 2c Wu CW, Sanborn TJ, Huang K, Zuckermann RN, Barron AE. J. Am. Chem. Soc. 2001; 123: 6778 2d Shin SB. Y, Yoo B, Todaro L, Kirshenbaum K. J. Am. Chem. Soc. 2007; 129: 3218 2e Wu CW, Kirshenbaum K, Sanborn TJ, Patch JA, Huang K, Dill KA, Zuckermann RN, Barron AE. J. Am. Chem. Soc. 2003; 125: 13525 2f Gorske BC, Bastian BL, Geske GD, Blackwell HE. J. Am. Chem. Soc. 2007; 129: 8928 2g Shah NH, Butterfoss GL, Nguyen K, Yoo B, Bonneau R, Rabenstein DL, Kirshenbaum K. J. Am. Chem. Soc. 2008; 130: 16622 2h Stringer R, Crapster JA, Guzei IA, Blackwell E. J. Org. Chem. 2010; 75: 6068 2i Paul B, Butterfoss GL, Boswell MG, Huang ML, Bonneau R, Wolf C, Kirshenbaum K. Org. Lett. 2012; 14: 926 2j Paul B, Butterfoss GL, Boswell MG, Renfrew PD, Yeung FG, Shah NH, Wolf C, Bonneau R, Kirshenbaum K. J. Am. Chem. Soc. 2011; 133: 10910 2k Roy O, Caumes C, Esvan Y, Didierjean C, Faure S, Taillefumier C. Org. Lett. 2013; 15: 2246 3 Maayan G, Ward MD, Kirshenbaum K. Proc. Natl. Acad. Sci. U.S.A. 2009; 106: 13679 4 Zuckermann RN, Kerr JM, Kent SB. H, Moos WH. J. Am. Chem. Soc. 1992; 114: 10646 5a Jang HJ, Fafarman A, Holub JM, Kirshenbaum K. Org. Lett. 2005; 7: 1951 5b Holub JM, Jang H, Kirshenbaum K. Org. Biomol. Chem. 2006; 4: 1497 5c Norgren AS, Budke C, Majer Z, Heggemann C, Koop T, Sewald N. Synthesis 2009; 488 5d Fürniss D, Mack T, Hahn F, Vollrath SB. L, Koroniak K, Schepers U, Bräse S. Beilstein J. Org. Chem. 2013; 9: 56 6a Maayan G, Yoo B, Kirshenbaum K. Tetrahedron Lett. 2008; 49: 335 6b Maayan G, Ward M, Kirshenbaum K. Chem. Commun. 2009; 56 7 Maayan G, Liu L.-K. Pept. Sci. 2011; 96: 679 8 Urankar D, Pinter B, Pevec A, De Proft F, Turel I, Košmrlj J. Inorg. Chem. 2010; 49: 4820 9 Crowley JD, Bandeen PH, Hanton LR. Polyhedron 2010; 29: 70 10 Vellas SK, Lewis JE. M, Shankar M, Sagatova A, Tyndall JD. A, Monk BC, Fitchett CM, Hanton LR, Crowley JD. Molecules 2013; 18: 6383 11 Schweinfurth D, Pattacini R, Strobel S, Sarkar B. Dalton Trans. 2009; 9291 12 Urankar D, Pevec A, Košmrlj J. Eur. J. Inorg. Chem. 2011; 1921 13 Kilpin KJ, Gavey EL, McAdam C, Anderson CB, Lind SJ, Keep CC, Gordon KC, Crowley JD. Inorg. Chem. 2011; 50: 6334 14 Happ B, Friebe C, Winter A, Hager MD, Hoogenboom R, Schubert US. Chem. Asian J. 2009; 4: 154 15 Bratsos I, Urankar D, Zangrando E, Genova-Kalou P, Košmrlj J, Alessio E, Turel I. Dalton Trans. 2011; 40: 5188 16 Fletcher JT, Bumgarner BJ, Engels ND, Skoglund DA. Organometallics 2008; 27: 5430 17 Obata M, Kitamura A, Mori A, Kameyama C, Czaplewska JA, Tanaka R, Kinoshita I, Kusumoto T, Hideki H, Harada M, Mikata Y, Funabikig T, Yano S. Dalton Trans. 2008; 3292 18 Copper Complexes; General MethodThe four copper(II) complexes were prepared by adding solid Cu(OAc)2 (1.2 equiv.) a 5.5 M solution of 6-PyrT2 or 6-PicT2 in MeOH (1 equiv) or solid Cu(OAc)2 (0.6 equiv) to a 5.5 M solution of 7-PyrT1 or 7-PicT1 in MeOH (1 equiv). The resulting solutions were stirred for 4 h and then the unreacted Cu salt was removed by filtration to give a green–blue filtrate. The solution was divided into two portions, and one portion was used for spectroscopic analysis. The other portion was evaporated under a low pressure and the solid obtained was washed with H2O (3 × 0.5 mL), and dried under low pressure. 19 Sakaguchi U, Addison AW. J. Chem. Soc., Dalton Trans. 1979; 600 Zusatzmaterial Zusatzmaterial Supporting Information
