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An efficient [3]catenane formation in a dynamic combinatorial library Jianwei Li and Sijbren Otto University of Groningen, Centre for System Chemistry, Stratingh Institute, Nijenborgh 4, 9747 AG Groningen, The Netherlands E-mail: Jianwei.li@rug.nl Catenanes, consisting of two or more interlocked macrocyclic rings, often exhibit markedly novel properties 1 . Although there are several strategies to synthesize this kind of molecules, synthetic challenges still remain 1 . Dynamic combinatorial chemistry is a useful tool to explore synthetic receptors and ligands for biomolecules 2 . Dynamic combinatorial libraries (DCLs) are produced by linking building blocks together using a reversible reaction, resulting in a thermodynamically controlled product distribution. Addition of a guest or a biomolecule shifts the distribution to those library members that bind best to the external target; a process referred to as templating. Considering the interaction between cyclodextrin homologues and azobenzene derivatives is strong, we set up a library using β-cyclodextrin and a dithiol-azobenzene derivative. We have found that two molecules of β-cyclodextrin were interlocked on one disulfide bonds linking tetramer macrocycle. The yield of the [3]catenane formation is 95%. This efficient synthesis of catenane by is proved by HPLC/MS and 1 H NMR. These results provide a new strategy for synthesizing catenane. 1. O. S. Miljanic, J. R. Heath and J. F. Stoddart, J. Am. Chem. Soc., 2007, 129, 8236-8246. 2. (a) P. T. Corbett, J. Leclaire, L. Vial, K. R. West, J. L. Wietor, J. K. M. Sanders and S. Otto, Chem. Rev. 2006, 106, 3652-3711. (b) R. A. R. Hunt and S. Otto, Chem. Commun. 2011, 47, 847-858.
HPLC study of the complexation of calix[4]arenephosphonic acids with amino acids O HO P HO Kalchenko O.I., Cherenok S.O., Yushchenko O.A., Kalchenko V.I. OH OH OPr PrO OH Institute of Organic Chemistry, National Academy of Sciences of Ukraine02660, Kiev-94, Ukraine, E-mail vik@ioch.kiev.ua Calix[n]arenes [1] composed of phenolic units linked via methylene groups have been studied as cavity-shaped host molecules able to recognize a wide range of guest molecules. It was shown by HPLC method calixarenes form supramolecular complexes with amino acids [2-4]. Binding constants of calixarenephosphonic acids 1-5 complexes with amino acids (Gly, Pro, Arg, Ala, Phe, Tyr, Trp) and tetrapeptide (Gly-Pro-Arg-Pro) in solution had been determined by high-performance liquid chromatohraphy (HPLC) in water- organic solution. O HO P HO OH OH OPr PrO OPr 3 HO HO O HO P HO OH OH OPr PrO OH P OH O HO HO O HO P HO OH OPr OPrPrO OPr P OH 1 2 3 4 5 Binding constants of the calixarene complexes (1:1) with аmіno acids were within the region 16000-48000 M -1 . Molecular modelling of the calixarene complexes were performed. The factors influencing the calixarene complexation: a) Conformation and hydrophobicity of calixarene-Host cavity; b) Nature and quantity of the substituents at the upper and the lower calixarene rim; c) Nature, size and quantity of the substituents in the Guest molecules, size and structure of the Guest molecules. It was established the correlation between KA amino acids. 1. Gutsche, C.D. (2008). Calixarenes revisited; The Royal Society of Chemistry, Cambridge, England. 2. Kalchenko O.I., Perret F., Coleman A.W. J. Chem. Soc. Perkin Trans. 2. 258 (2001). 3. Kalchenko O.I., Da Silva E., Coleman A.W. J. Incl. Phenom., 43, 305 (2002). 4. Kalchenko O.I., Cherenok S.O., Rodik R.V., Drаpаilo A.B., Міrоshnichеnkо S.I., Kаlchеnkо V.I. Phosphorus, Sulfur, and Silicon, In press. O O HO P HO HO O O OH HO P HO P HO O OPr OPr PrO OPr P OH OH P OH of the calixarene complexes and properties of HO HO P O O P O H OH OH P OH O
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4 th International Summer School Se
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4 th International Summer School
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Tuesday, September 13 th 9 - 10.30
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4.30 - 5.30 pm Poster Short Talks (
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2.30 - 4 pm Session VIII (Inorganic
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11.30 - 12.00 am Olga Federova, Mos
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INNOVATIVE DEVELOPMENTS ON THE BASI
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Calixarenes: from molecular recepto
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Controlled and Targeted Drug Delive
Page 19 and 20: What does the recognition of biomol
Page 21 and 22: Binding properties of calix[4]arene
Page 23 and 24: “Light and Molecular Design in Bi
Page 25 and 26: Supramolecular protein immobilizati
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Page 29 and 30: Chiral Concave N-Heterocyclic Carbe
Page 31 and 32: Aromaticity Switching In Porphyrino
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Page 37 and 38: Polyphosphorus Ligands in Supramole
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Page 41 and 42: Luisa De Cola Germany, Münster "Se
Page 43 and 44: Cationic amphiphilic calixarenes: s
Page 45 and 46: Supramolecular devices based on pho
Page 47 and 48: The sensing of interfacial interact
Page 49 and 50: Molecular recognition of organic qu
Page 51 and 52: Towards a molecular assembly based
Page 53 and 54: Analysis of benzodiaza-15-crown-5 e
Page 55 and 56: Crown-containing derivatives of nap
Page 57 and 58: Tuning of Knoevenagel-type substrat
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Page 61 and 62: Synthesis and supramolecular associ
Page 63 and 64: The features of the coordination ne
Page 65 and 66: Catalysts within Dynamic Combinator
Page 67 and 68: SYNTHESIS AND COMPLEXATION ABILITIE
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Page 75 and 76: SYNTHETIC TETRAAMIDES ANION RECEPTO
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Page 79 and 80: Catechol derivatives of thiacalix[4
Page 81 and 82: Victor Pavlovsky Ukraine, Odessa "S
Page 83 and 84: Synthesis of disubstituted by merca
Page 85 and 86: SUPRAMOLECULAR POLYMERS OF OLIGO-DY
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Page 89 and 90: Conjugates of thiacalixarenes and c
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