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

Micke Lisbjerg; Bo M. Jessen; Brian Rasmussen; Bjarne Enrico Nielsen; Anders Østergaard Madsen; Michael Pittelkow

doi:10.1039/c4sc00990h

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

Micke Lisbjerg, Bo M. Jessen, Brian Rasmussen, Bjarne Enrico Nielsen, Anders Østergaard Madsen, Michael Pittelkow^*

^*Corresponding author for this work

Department of Chemistry

67 Citations (Scopus)

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.

Original language	English
Journal	Chemical Science
Volume	5
Issue number	7
Pages (from-to)	2647-2650
Number of pages	4
ISSN	2041-6520
DOIs	https://doi.org/10.1039/c4sc00990h
Publication status	Published - 2014

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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.",

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AU - Lisbjerg, Micke

AU - Jessen, Bo M.

AU - Rasmussen, Brian

AU - Nielsen, Bjarne Enrico

AU - Madsen, Anders Østergaard

AU - Pittelkow, Michael

PY - 2014

Y1 - 2014

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AB - 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.

U2 - 10.1039/c4sc00990h

DO - 10.1039/c4sc00990h

M3 - Journal article

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VL - 5

SP - 2647

EP - 2650

JO - Chemical Science

JF - Chemical Science

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ER -

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

Abstract

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