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Synlett 2009(17): 2875-2879  
DOI: 10.1055/s-0029-1217988
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Potential Supramolecular Cyclodextrin Dimers Using Nucleobase Pairs

Florian Hamona, Bruno Violeaua, Frédéric Turpinb, Mathilde Bellotc, Laurent Bouteillerc, Florence Djedaini-Pilardd, Christophe Len*a
a Université de Poitiers, UMR 6514 CNRS, Synthèse et Réactivité des Substances Naturelles, 40 Avenue du Recteur Pineau, 86022 Poitiers Cedex, France
Fax: +33(5)49453501; e-Mail: christophe.len@univ-poitiers.fr;
b Biocydex, 40 Avenue du Recteur Pineau, 86022 Poitiers Cedex, France
c Université Paris 6, UMR 7610 CNRS, 4 Place Jussieu, 75252 Paris, France
d Université de Picardie Jules Verne, UMR 6219 CNRS, Laboratoire des Glucides, 33 Rue Saint Leu, 80039 Amiens, France
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Publikationsverlauf

Received 11 June 2009
Publikationsdatum:
24. September 2009 (online)

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Abstract

The synthesis of six new cyclodextrin derivatives having nucleobase moiety is described. These two moieties are linked by different spacers, such as aminoethyl and 1,2,3-triazolyl groups. Example of association constants for complexation of adenine and thymine derivatives: K AT = 385 M-¹ using NMR methodology is reported. Study of interaction between four cyclodextrin derivatives and one adamantyl guest is described by ITC.

Key words

click chemistry - nucleobase - cyclodextrin

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28

Selected Physical Data of Compound 8a
MP 200 ˚C (decomp.). ¹H NMR (500 MHz, D2O): δ = 7.48 (s, 1 H), 5.14-5.08 (m, 7 H), 4.30-4.10 (m, 3 H), 4.03-3.81 (m, 25 H), 3.72-3.50 (m, 15 H), 3.47 (m, 2 H), 3.39 (m, 1 H), 1.91 (s, 3 H) ppm. ¹³C NMR (125 MHz, D2O): δ = 166.8, 153.0, 142.2, 111.5, 102.0-101.0, 83.3-80.8, 71.5-70.5, 67.5, 60.5-59.5, 48.8, 47.6, 45.0, 11.3 ppm. ESI-HRMS: m/z calcd [M + H]+: 1286.4522; found: 1286.4581.

29

Selected Physical Data of Compound 8b
Mp 200 ˚C (decomp.). ¹H NMR (500 MHz, D2O): δ = 7.56 (s, 1 H), 5.36-5.24 (m, 5 H), 4.00 (s, 2 H), 3.89-3.54 (m, 33 H), 3.64-3.62 (m, 21 H), 3.55-3.52 (m, 21 H), 3.43-3.37 (m, 7 H), 3.41-3.40 (m, 21 H), 3.23 (br s, 2 H), 3.18 (br s, 2 H), 1.94 (s, 3 H) ppm. ¹³C NMR (125 MHz, D2O): δ = 166.8, 152.4, 143.1, 110.6, 97.6-96.6, 81.4-75.9, 71.2-69.6, 59.9-58.1, 48.5, 47.4, 47.0, 11.43 ppm. ESI-HRMS: m/z calcd
[M + H]+: 1566.7532; found: 1565.7573.
Selected Physical Data of Compound 9a
Mp 200 ˚C (decomp.). ¹H NMR (500 MHz, D2O): δ = 8.52 (s, 1 H), 8.40 (s, 1 H), 5.17-5.10 (m, 7 H), 4.38 (s, 2 H), 4.00-3.50 (m, 39 H) 3.31 (t, 1 H), 3.11 (m, 2 H), 2.95 (d,
1 H), 2.77 (m, 1 H) ppm. ¹³C NMR (125 MHz, D2O): δ = 155.4, 152.2, 149.5, 142.5, 118.5, 102.0-101.7, 101.0, 83.5, 81.2-80.1, 73.1-70.2, 60.3-59.9, 48.2, 47.0, 43.2 ppm. ESI-HRMS: m/z calcd [M + H]+: 1295,4637; found: 1295.4574.
Selected Physical Data of Compound 9b
Mp 200 ˚C (decomp.). ¹H NMR (500 MHz, D2O): δ = 8.31 (s, 1 H), 8.23 (s, 1 H), 5.29-5.24 (m, 5 H), 5.17 (s, 1 H), 4.98 (s, 1 H), 4.44 (br s, 2 H), 3.88-3.51 (m, 26 H), 3.64-3.62 (m, 21 H), 3.55-3.52 (m, 21 H), 3.41-3.32 (m, 14 H), 3.41-3.40, (m, 21 H), 3.24 (br s, 2 H), 3.05 (br s, 2 H) ppm. ¹³C NMR (125 MHz, D2O): δ = 155.5, 152.4, 149.3, 142.6,118.5, 97.7-96.5, 80.9-76.5, 71.1-70.7, 60.0-58.0, 48.1, 47.5, 43.2 ppm. ESI-HRMS: m/z calcd [M + H]+: 1575.7673; found: 1575.7654.

30

Selected Physical Data of Compound 11
Mp 200 ˚C (decomp.). ¹H NMR (500 MHz, D2O): δ = 8.10 (s, 1 H), 7.66 (s, 1 H), 5.20 (s, 1 H), 5.10-5.03 (m, 9 H), 4.63 (s, 1 H), 4.30 (s, 1 H), 4.08-3.50 (m, 37 H), 3.01 (s, 1 H), 2.70 (s, 1 H), 1.92 (s, 3 H) ppm. ¹³C NMR (125 MHz, D2O): δ = 167.1, 152.2, 142.4, 126.5, 111.2, 101.9-101.4, 83.2-80.5, 73.0-70.4, 60.3, 59.1, 51.4, 42.9, 11.3 ppm. ESI-HRMS: m/z calcd [M + Na+]: 1346.4246; found: 1346.4211.

31

Selected Physical Data of Compound 12
Mp 200 ˚C (decomp.). ¹H NMR (500 MHz, D2O): δ = 8.29 (s, 1 H), 8.26 (s, 1 H), 7.99 (s, 1 H), 5.60 (s, 2 H), 5.15-5.00 (m, 7 H), 4.97 (d, 1 H), 4.59 (dd, 1 H), 4.11 (t, 1 H), 4.00-3.40 (m, 37 H), 2.78 (d, 1 H), 2.60 (d, 1 H) ppm. ¹³C NMR (125 MHz, D2O): δ = 155.6, 152.7, 148.9, 142.6, 142.1, 125.9, 118.6, 101.9, 81.3-80.4, 73.1-70.6, 60.0-58.8, 51.2, 38.4 ppm. ESI-HRMS: m/z calcd [M + Na+]: 1355.4362; found: 1355.4363.