GenZ binders

Generation Zero (GenZ) set of supramolecular biomimetic binders (SBBs) is the foundation stone of the calixDNA project. It consists of calix[4]arene and calix[6]arene derivatives with variety of substituents on both narrow and large rim of the calixarene basket. These remarkable compounds, developed over past two decades in the group of the calixDNA team member Olivia Reinaud at the University of Paris (formerly Descartes University in Paris).

MethylImidazole containing gen_Z BINDERS

Syntheses:

  • SBB 1, X4Me2ImMe2(NH2)2[1]
  • SBB 2, X4Me2ImMe2(TZMeNMe3+)2[1]
  • SBB 3, X6Me3ImMe3(NH2)3[2]
  • SBB 4, X6Me3ImMe3(TZMeNMe3+)3[2]

[1] A. Maurin, S. Varatharajan, B. Colasson, O. Reinaud, Org. Lett. 16 (2014) 5426 – 5429.

[2] O. Bistri, B. Colasson, O. Reinaud, Chem. Sci. 3 (2012) 811–818.

TMPA CAPPED gen_Z BINDERS

Syntheses:

  • SBB 5, X6Me3TMPA(NH2)3[3]
  • SBB 5a, X6Me3TMPA
  • SBB 6, X6Me3TMPA(NH2)6HPF6[4]
  • SBB 7, X6Me3TMPA(NMe3+)3[3]

[3] G. Thiabaud, A. Brugnara, M. Carboni,N. Le Poul, B. Colasson, Y. Le Mest, O. Reinaud, Org. Lett. 14 (2012) 2500 – 2503.

[4] Synthesis of the hexanitro precursor: A. Brugnara, L. Fusaro, M. Luhmer, T.Prangé, B. Colasson, O. Reinaud, Org. Biomol. Chem., 12 (2014) 2754; Synthesis of the 6:HPF6 adduct with the protonated TMPA cap: A. Brugnara: Contrôle cavitaire de la réactivité redox d’un ion métallique (Cu) dans un environnement biomimétique, PhD thesis, supervisor: O. Reinaud, University of Paris, 2013, p. 220.

TREN CAPPED GEN_Z BINDERS
TREN (tris-2-aminoethyl-amine) capped supramolecular biomimetic binders at narrow rim (nr, up) and at large rim (lr, down)
  • X6Me3TRENnr[5]
  • X6TRENnr[6]
  • X6Me3TRENnr(NH2)3[7]
  • X6Me6TRENlr[8]
  • X6Me3TRENamidlr[9]

[5] I. Jabin, O. Reinaud, J. Org. Chem.68(2003) 3416−3419.

[6] G. De Leener, D. Over, O. Reinaud, I. Jabin: Turning on anion and betaine hosting by a small structural change of a biomimetic cavity: a case study, Superamolecular chemistry (2022) just accepted.

[7] A. Inthasot, E. Brunetti, M. Lejeune, N. Menard, T. Prange, L. Fusaro, L. G. Bruylants, O. Reinaud, M. Luhmer, I. Jabin, B. Colasson, Chem. – Eur. J. 22 (2016) 4855 – 4862.

[8] S. Zahim, L. A. Wickramasinghe, G. Evano, I. Jabin, R. Schrock, P. Müler, Org. Lett. 18 (2016) 1570−1573l.

[9] N. Nyssen, D. Ajami, A. Ardelean, F. Desroches, J. Li, M. Luhmer, O. Reinaud, I. Jabin, JOC 86, 17  (2021) 12075-12083.

OTHER BINDERS

        

  • X6Me3EtCOOH3(NH3Cl)3 [10]
  • X6Me3(EtNH2)3 [11]

[10] A. Inthasot, M.-D. Dang Thy, M. Lejeune, L. Fusaro, O. Reinaud, M. Luhmer, B. Colasson, I. Jabin, JOC, 79 (2014) 1913 – 1919.

[11] U. Darbost, M. Giorgi, O. Reinaud, I. Jabin, JOC, 69, 15 (2004) 4879 – 4884.

METAL COMPLEXES