An Acyclic Aminonaphthyridine‐Based Receptor for Carbohydrate Recognition: Binding Studies in Competitive Solvents

An Acyclic Aminonaphthyridine‐Based Receptor for Carbohydrate Recognition: Binding Studies in Competitive Solvents
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用于碳水化合物识别的无环氨基萘啶受体:竞争性溶剂中的结合研究

DOI:
10.1002/ejoc.200700264
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发表时间:
2007
影响因子:
2.8
通讯作者:
Hüseyin Cavga
Hüseyin Cavga
中科院分区:
化学3区
文献类型:
--
作者:
M. Mazik;Hüseyin Cavga

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1H NMR光谱和微量量热滴定表明,受体3b,由三个质子化的2-氨基-1,8-萘啶单元,结合N-乙酰神经氨酸(Neu 5Ac),最常见的唾液酸,在竞争性溶剂,如水/二甲亚砜的高亲和力。受体3b能够与Neu 5Ac形成中性/电荷增强的氢键和离子对,类似于唾液酸结合蛋白。此外,通过NMR光谱提供了中性糖如甲基β-D-吡喃葡萄糖苷、D-麦芽糖和D-纤维二糖的弱结合的指示。分子模拟计算,合成和结合研究在水介质中进行了描述。(© Wiley-VCH Verlag GmbH & Co. KGaA,69451魏因海姆,德国,2007)
1H NMR spectroscopic and microcalorimetric titrations revealed that receptor 3b, consisting of three protonated 2-amino-1,8-naphthyridine units, binds N-acetylneuraminic acid (Neu5Ac), the most commonly occurring sialic acid, with high affinity in competitive solvents such as water/dimethyl sulfoxide. Receptor 3b is able to form neutral/charge-reinforced hydrogen bonds and ion pairs with Neu5Ac, similar to sialic acid-binding proteins. Furthermore, indications for weak binding of neutral sugars, such as methyl β-D-glucopyranoside, D-maltose and D-cellobiose were provided by NMR spectroscopy. Molecular modelling calculations, synthesis and binding studies in aqueous media are described. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
DOI: 10.1021/ja064012h
发表时间: 2006-09-20
影响因子: 15
作者:
Sessler, Jonathan L.;Gross, Dustin E.;Gale, Philip A.
通讯作者: Gale, Philip A.