Discovery of a cyclic 6+6 hexamer of D-biotin and formaldehyde

被引：93

作者：

Lisbjerg, Micke ^{[1
]}

Jessen, Bo M. ^{[1
]}

Rasmussen, Brian ^{[1
]}

Nielsen, Bjarne E. ^{[1
]}

Madsen, Anders O. ^{[1
]}

Pittelkow, Michael ^{[1
]}

机构：

[1] Univ Copenhagen, Dept Chem, DK-2100 Copenhagen, Denmark

来源：

CHEMICAL SCIENCE | 2014年 / 5卷 / 07期

关键词：

RING;

D O I：

10.1039/c4sc00990h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The discovery of receptors using templated synthesis enables the selection of strong receptors from complex mixtures. In this contribution we describe a study of the condensation of D-biotin and formaldehyde in acidic water. We have discovered that halide anions template the formation of a single isomer of a 6 + 6 macrocycle. The macrocycle (biotin[6] uril) is water-soluble, chiral and binds halide anions (iodide, bromide and chloride) with selectivity for iodide in water, and it can be isolated on a gram scale in a one-pot reaction in 63% yield.

引用

页码：2647 / 2650

页数：4

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