Synlett 2015; 26(04): 461-466
DOI: 10.1055/s-0034-1378938
letter
© Georg Thieme Verlag Stuttgart · New York

Click 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
› Author Affiliations
Further Information

Publication History

Received: 08 September 2014

Accepted after revision: 20 October 2014

Publication Date:
21 November 2014 (online)


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).

Supporting Information

 
  • 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