Issue 7, 2014

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


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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Article information

Article type
Edge Article
04 Apr 2014
21 Apr 2014
First published
22 Apr 2014
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2014,5, 2647-2650

Author version available

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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