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Enantioselective Activity of Hemin in Supramolecular Gels Formed by Co‐Assembly with a Chiral Gelator
Author(s) -
Wang Song,
Jiang Hejin,
Zhang Li,
Jiang Jian,
Liu Minghua
Publication year - 2018
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201800390
Subject(s) - hemin , supramolecular chemistry , enantioselective synthesis , supramolecular chirality , chirality (physics) , supramolecular catalysis , chemistry , catalysis , combinatorial chemistry , supramolecular assembly , non covalent interactions , stereochemistry , crystallography , organic chemistry , heme , hydrogen bond , molecule , enzyme , crystal structure , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark
Supramolecular co‐assembly provides an efficient way to combine structural and functional units through noncovalent interactions and produce materials with enhanced performance. Here, using a chiral amphiphilic histidine derivative (LHC18 or DHC18) as a gelator, we have successfully co‐assembled the gelator and hemin through gelation. During the co‐assembly, the chiral information of the gelator was transcribed into the assemblies, and thus right‐ and left‐handed helical ribbons from LHC18‐Hemin and DHC18‐Hemin co‐assemblies were obtained, respectively, which were confirmed by CD spectra and SEM observations. These helical ribbons were used as artificial enzymes to catalyse the oxidation reaction of 3,4‐dihydroxy‐L‐phenylalanine (L‐DOPA). The catalytic activity of hemin in supramolecular gels can be effectively enhanced over that of free hemin. Moreover, by virtue of induced chirality, the supramolecular gels of LHC18‐Hemin and DHC18‐Hemin exhibited obvious enantioselective activity. This work provides a way to combine chirality transfer and supramolecular asymmetric catalysis.