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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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Supplementary files

Article information


Submitted
04 Apr 2014
Accepted
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

Chem. Sci., 2014,5, 2647-2650
Article type
Edge Article
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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