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

被引：23

作者：

Mibu, Nobuko ^{[1
]}

Aki, Hatsumi ^{[1
]}

Ikeda, Hirohito ^{[1
]}

Saito, Ai ^{[1
]}

Uchida, Wataru ^{[1
]}

Yokomizo, Kazumi ^{[2
]}

Zhou, Jianrong ^{[2
]}

Miyata, Takeshi ^{[2
]}

Sumoto, Kunihiro ^{[1
]}

机构：

[1] Fukuoka Univ, Fac Pharmaceut Sci, Jonan Ku, Fukuoka 8140180, Japan

[2] Sojo Univ, Fac Pharmaceut Sci, Kumamoto 8620082, Japan

来源：

JOURNAL OF THERMAL ANALYSIS AND CALORIMETRY | 2013年 / 113卷 / 03期

关键词：

Carbohydrate recognition; Tris(2-aminoethyl)amine; Tripodal receptor; Methyl alpha-D-mannopyranoside; Calorimetry; Complex; BIOLOGICAL-ACTIVITIES; AFFINITY;

D O I：

10.1007/s10973-012-2813-5

中图分类号：

O414.1 [热力学];

学科分类号：

摘要：

Carbohydrate recognition of some bioactive symmetrical tripodal receptor type tris(2-aminoethyl)amine (TAEA) derivatives was investigated. In calorimetric experiments, the highest binding constant (Ka) of compound C (C35H49N5O4S) with methyl alpha-d-mannopyranoside was Ka = 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 a dagger HA degrees (=-34 to -511 kJ mol(-1)). In a comparison of each set of alpha- and beta-anomers of some monosaccharides (methyl alpha/beta-d-galactopyranoside, methyl alpha/beta-d-glucopyranoside, and methyl alpha/beta-l-fucopyranoside), compound C showed that the binding constant of beta-anomer was larger than that of the corresponding alpha-anomer, indicating higher beta-anomer selectivity. The calculated energy-minimized structure of the complex of compound C with guest methyl alpha-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.

引用

页码：1015 / 1018

页数：4

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