Discovery of a cyclic 6 + 6 hexamer of d-biotin and formaldehyde
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Discovery of a cyclic 6 + 6 hexamer of d-biotin and formaldehyde. / Lisbjerg, Micke; Jessen, Bo M.; Rasmussen, Brian; Nielsen, Bjarne Enrico; Madsen, Anders Østergaard; Pittelkow, Michael.
In: Chemical Science, Vol. 5, No. 7, 2014, p. 2647-2650.Research output: Contribution to journal › Journal article › Research › peer-review
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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
VL - 5
SP - 2647
EP - 2650
JO - Chemical Science
JF - Chemical Science
SN - 2041-6520
IS - 7
ER -
ID: 130988244