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1 Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014 Supporting informations Diastereoselective recognition of -mannoside by hemicryptophane receptors Aline Schmitt, Bastien Chatelet, Daniele Padula, Lorenzo Di Bari, Jean-Pierre Dutasta* and Alexandre Martinez* Laboratoire de Chimie, Ecole Normale Supérieure de Lyon, CNRS, UCBL, 46, Allée d Italie, Lyon, France Institute of Organic Chemistry and Biochemistry, Academy of Sciences, Flemingovo náměstí 2, Prague, Czech Republic Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via Risorgimento 35, I Pisa, Italy alexandre.martinez@ens-lyon.fr jean-pierre.dutasta@ens-lyon.fr Table of Contents A) NMR spectra 2 1) M-SSS-3 2 2) P-SSS-3 3 3) P-RRR-3 4 4) M-RRR-3 5 B) Mass spectra 6 C) 1 H NMR titration 7 Figure S-1 1 H NMR titration curves for the complexation of the carbohydrates by 3 7 reports for the determination of the K a values 8 D) Computational Details 12 E) Bibliography 13 1
2 A) NMR spectra 1) M-SSS-3 1 H NMR (CDCl 3, 298 K, MHz): H 2 O 13 C NMR (CDCl 3, 298 K, MHz): 2
3 2) P-SSS-3 1 H NMR (CDCl 3, 298 K, MHz): H 2 O acetone 13 C NMR (CDCl 3, 298 K, MHz): acetone 3
4 3) P-RRR-3 1 H NMR (CDCl 3, 298 K, MHz): acetone H 2 O 13 C NMR (CDCl 3, 298 K, MHz): acetone 4
5 4) M-RRR-3 1 H NMR (CDCl 3, 298 K, MHz): H 2 O acetone 13 C NMR (CDCl 3, 298 K, MHz): Et 3 N acetone 5
6 B) Masse spectra 1) M-SSS-3 2) P-SSS-3 6
7 C) 1 H NMR titration 0-0,002-0,004-0,006-0,008-0,01-0, Δδ (ppm) [galactoside] 0 /[3] 0 OctαGal@P-RRR-7 3 OctαGal@M-SSS-7 3 OctαGal@P-SSS-7 3 OctαGal@M-RRR-7 3 OctβGal@M-SSS-7 3 OctβGal@P-SSS-7 3 OctβGal@P-RRR-7 3 OctβGal@M-RRR-7 3 [mannoside] 0 /[3] 0-0, ,008-0,013-0,018-0,023-0,028 Δδ (ppm) OctαMan@M-SSS-7 3 OctβMan@M-SSS-7 3 OctαMan@P-SSS-7 3 OctβMan@P-SSS-7 3 OctαMan@P-RRR-7 3 OctβMan@P-RRR-7 3 OctαMan@M-RRR-7 3 OctβMan@M-RRR-7 3 7
8 -0,0025-0,0065-0,0105-0,0145 [glucoside] 0 /[3] OctαGlu@M-SSS-7 3 OctαGlu@P-SSS-7 3 OctβGlu@M-SSS-7 3 OctβGlu@P-SSS-7 3 octαglu@p-rrr-7 3 OctαGlu@M-RRR-7 3 octβglu@p-rrr-7 3 OctβGlu@M-RRR-7 3-0,0185 Δδ (ppm) Figure S-1 1 H NMR titration curves for the complexation of the carbohydrates by 3 (Complexation induced shifts of either the OMe or the aromatic protons of the linkers were plotted as a function of the guest/host ratio; dots correspond to experimental data and the curves are those obtained after modeling by HypNMR 2008 with a model based on the formation of a 1:1 complex) reports for the determination of the K a values Receptor: M-SSS-3 guest: OctαMan Converged in 5 iterations with sigma = 0, log beta(hcsucre) (4) Receptor: M-SSS-3 guest: OctβMan Converged in 4 iterations with sigma = 0, log beta(hcsucre) (2) Receptor: P-SSS-3 guest: OctαMan Converged in 5 iterations with sigma = 0, log beta(hcsucre) (2) 8
9 Receptor: P-SSS-3 guest: OctβMan Converged in 1 iterations with sigma = 0, log beta(hcsucre) (4) Receptor: P-RRR-3 guest: OctαMan Converged in 6 iterations with sigma = 0, log beta(hcsucre) (3) Receptor: P-RRR-3 guest: OctβMan Converged in 6 iterations with sigma = 0, log beta(hcsucre) (5) Receptor: M-RRR-3 guest: OctαMan Converged in 4 iterations with sigma = 0, log beta(hcsucre) (2) Receptor: M-RRR-3 guest: OctβMan Converged in 5 iterations with sigma = 0, log beta(hcsucre) (4) Receptor: M-SSS-3 guest: OctαGlc Converged in 5 iterations with sigma = 0, log beta(hcsucre) (4) 9
10 Receptor: M-SSS-3 guest: OctβGlc Converged in 1 iterations with sigma = 0, log beta(hcsucre) (4) Receptor: P-SSS-3 guest: OctαGlc Converged in 4 iterations with sigma = 0, log beta(hcsucre) (4) Receptor: P-SSS-3 guest: OctβGlc Converged in 4 iterations with sigma = 0, log beta(hcsucre) (4) Receptor: P-RRR-3 guest: OctαGlc Converged in 4 iterations with sigma = 0, log beta(hcsucre) (5) Receptor: P-RRR-3 guest: OctβGlc Converged in 1 iterations with sigma = 0, log beta(hcsucre) (6) Receptor: M-RRR-3 guest: OctαGlc Converged in 4 iterations with sigma = 0, log beta(hcsucre) (8) 10
11 Receptor: M-RRR-3 guest: OctβGlc Converged in 4 iterations with sigma = 0, log beta(hcsucre) (1) Receptor: M-SSS-3 guest: OctαGal Converged in 5 iterations with sigma = 0, log beta(hcsucre) (1) Receptor: M-SSS-3 guest: OctβGal Converged in 6 iterations with sigma = 0, beta(hcsucre) -6.2E Log beta cannot be updated Receptor: P-SSS-3 guest: OctαGal Converged in 5 iterations with sigma = 0, log beta(hcsucre) (8) Receptor: P-SSS-3 guest: OctβGal Converged in 4 iterations with sigma = 0, log beta(hcsucre) excessive relative error on beta = 41% 11
12 Receptor: P-RRR-3 guest: OctαGal Converged in 6 iterations with sigma = 0, log beta(hcsucre) (1) Receptor: P-RRR-3 guest: OctβGal Converged in 4 iterations with sigma = 0, log beta(hcsucre) (1) Receptor: M-RRR-3 guest: OctαGal Converged in 4 iterations with sigma = 0, log beta(hcsucre) (1) Receptor: M-RRR-3 guest: OctβGal Converged in 3 iterations with sigma = 0, log beta(hcsucre) (1) D) Computational Details Electronic TDDFT calculations were run using the Gaussian09 package 1 employing a set of different functionals (B3LYP, CAM-B3LYP, BH&HLYP) in combination with the SVP basis set on the first 36 excited states. Spectra were generated using the program SpecDis 2 by applying a Gaussian bandshape with exponential bandwith σ = 0.15 ev. The CD curves have been constructed using dipole-length computed rotatory strengths; dipole-velocity data differ by less than 10% for most transitions. 12
13 E) Bibliography 1. Gaussian 03: M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Jr. Montgomery, J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian, Wallingford, CT, T. Bruhn, A. Schaumlöffel, Y. Hemberger, G. Bringmann, Chirality 2013, 25,
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