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Issue 7, 2014
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Discovery of a cyclic 6 + 6 hexamer of D-biotin and formaldehyde

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Abstract

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.

Graphical abstract: Discovery of a cyclic 6 + 6 hexamer of d-biotin and formaldehyde

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Publication details

The article was received on 04 Apr 2014, accepted on 21 Apr 2014 and first published on 22 Apr 2014


Article type: Edge Article
DOI: 10.1039/C4SC00990H
Citation: Chem. Sci., 2014,5, 2647-2650
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    Discovery of a cyclic 6 + 6 hexamer of D-biotin and formaldehyde

    M. Lisbjerg, B. M. Jessen, B. Rasmussen, B. E. Nielsen, A. Ø. Madsen and M. Pittelkow, Chem. Sci., 2014, 5, 2647
    DOI: 10.1039/C4SC00990H

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