Carbohydrate recognition of symmetrical tripodal receptor type tris(2-aminoethyl)amine derivatives

• Published in: Journal of thermal analysis and calorimetry Vol. 113; no. 3; pp. 1015 - 1018
• Main Authors: Mibu, Nobuko, Aki, Hatsumi, Ikeda, Hirohito, Saito, Ai, Uchida, Wataru, Yokomizo, Kazumi, Zhou, Jianrong, Miyata, Takeshi, Sumoto, Kunihiro
• Format: Journal Article Conference Proceeding
• Language: English
• Published: Dordrecht Springer Netherlands 01.09.2013; Springer
• Subjects: Analytical Chemistry; Binding; Calorimetry; Carbohydrates; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides; Carbohydrates. Nucleosides and nucleotides; Chemistry; Chemistry and Materials Science; Derivatives; Exact sciences and technology; Inorganic Chemistry; Mathematical analysis; Measurement Science and Instrumentation; Organic chemistry; Physical Chemistry; Polymer Sciences; Preparations and properties; Receptors; Recognition; Stoichiometry; Carbohydrate recognition; Methyl α; Calorimetry; Tripodal receptor; Tris(2-aminoethyl)amine; mannopyranoside; Complex; Oligosaccharide; Stability constant; Thioureas; Complexes; Amine; Tripod; Glycoside; Thermal analysis; Methyl α-D-mannopyranoside; Thermodynamic properties; Chemical synthesis; Recognition
• ISSN: 1388-6150; 1588-2926; 1572-8943
• DOI: 10.1007/s10973-012-2813-5

Carbohydrate recognition of some bioactive symmetrical tripodal receptor type tris(2-aminoethyl)amine (TAEA) derivatives was investigated. In calorimetric experiments, the highest binding constant ( K a) of compound C (C 35 H 49 N 5 O 4 S) with methyl α- d -mannopyranoside was K a = 858 M −1 with 1:1 stoichiometry. Formation of hydrogen bonds in binding between symmetrical tripodal receptor type compound C and sugars was suggested by the large negative values of ∆ H ° (=−34 to −511 kJ mol −1 ). In a comparison of each set of α- and β-anomers of some monosaccharides (methyl α/β- d -galactopyranoside, methyl α/β- d -glucopyranoside, and methyl α/β- l -fucopyranoside), compound C showed that the binding constant of β-anomer was larger than that of the corresponding α-anomer, indicating higher β-anomer selectivity. The calculated energy-minimized structure of the complex of compound C with guest methyl α- d -mannopyranoside is also presented. The experimental results obtained from this work indicated that symmetrical tripodal receptor type TAEA derivative C has a lectin-like carbohydrate recognition property.