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 af dette arbejde

Kemisk Institut

67 Citationer (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.

Originalsprog	Engelsk
Tidsskrift	Chemical Science
Vol/bind	5
Udgave nummer	7
Sider (fra-til)	2647-2650
Antal sider	4
ISSN	2041-6520
DOI	https://doi.org/10.1039/c4sc00990h
Status	Udgivet - 2014

Adgang til dokumentet

10.1039/c4sc00990h

Citationsformater

@article{eb0d8c30e59549fca8a69599d9fa1f73,

title = "Discovery of a cyclic 6 + 6 hexamer of d-biotin and formaldehyde",

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.",

author = "Micke Lisbjerg and Jessen, {Bo M.} and Brian Rasmussen and Nielsen, {Bjarne Enrico} and Madsen, {Anders {\O}stergaard} and Michael Pittelkow",

year = "2014",

doi = "10.1039/c4sc00990h",

language = "English",

volume = "5",

pages = "2647--2650",

journal = "Chemical Science",

issn = "2041-6520",

publisher = "Royal Society of Chemistry",

number = "7",

}

TY - JOUR

T1 - Discovery of a cyclic 6 + 6 hexamer of d-biotin and formaldehyde

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

N2 - 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.

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

AN - SCOPUS:84901856569

SN - 2041-6520

VL - 5

SP - 2647

EP - 2650

JO - Chemical Science

JF - Chemical Science

IS - 7

ER -

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

Abstract

Adgang til dokumentet

Fingeraftryk

Citationsformater