A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä
Selective recognition of neutral guests in an aqueous medium by a biomimetic calix[6]cryptamide receptor (2016)
Lascaux, A., De Leener, G., Fusaro, L., Topic, F., Rissanen, K., Luhmer, M., & Jabin, I. (2016). Selective recognition of neutral guests in an aqueous medium by a biomimetic calix[6]cryptamide receptor. Organic and Biomolecular Chemistry, 14(2), 738-746. https://doi.org/10.1039/C5OB02067K
JYU-tekijät tai -toimittajat
Julkaisun tiedot
Julkaisun kaikki tekijät tai toimittajat: Lascaux, Angélique; De Leener, Gaël; Fusaro, Luca; Topic, Filip; Rissanen, Kari; Luhmer, Michel; Jabin, Ivan
Lehti tai sarja: Organic and Biomolecular Chemistry
ISSN: 1477-0520
eISSN: 1477-0539
Julkaisuvuosi: 2016
Volyymi: 14
Lehden numero: 2
Artikkelin sivunumerot: 738-746
Kustantaja: RSC Publications
Julkaisumaa: Britannia
Julkaisun kieli: englanti
DOI: https://doi.org/10.1039/C5OB02067K
Julkaisun avoin saatavuus: Ei avoin
Julkaisukanavan avoin saatavuus:
Tiivistelmä
The design of artificial receptors that can efficiently work in water is a challenging research area. A possible biomimetic approach for the elaboration of such receptors consists of associating a hydrophobic cavity with a polar polyfunctional binding site. On this basis, a hydrophilic calix[6]cryptamide decorated with oligo(ethylene glycol) units (i.e.8) was synthesized through an efficient [1 + 1] macrocyclization reaction as the key-step. The complexation of neutral molecules was evaluated by NMR spectroscopy through competition experiments either in apolar or aqueous media. In both media, host 8 can bind neutral species that display H-bonding acceptor and donor groups such as amides or ureas. Interestingly, the most polar and acidic molecule is the best guest in chloroform and the worst one in an aqueous medium, highlighting the importance of the environment. As shown by NMR and X-ray diffraction data, the mode of recognition involves a complementary DAAAD-ADDDA quintuple H-bonding array between the binding partners as well as multiple CH–π interactions. A comparison of this calix[6]arene-based host–guest system with the binding site of biotin-binding proteins shows strong similarities. Besides, the acid–base control of the binding properties of receptor 8 in aqueous media is highly reminiscent of allosteric processes encountered in natural systems.
Vapaat asiasanat: artificial receptors; biomimetics; aqueous medium
Liittyvät organisaatiot
Hankkeet, joissa julkaisu on tehty
- Heikot vuorovaikutukset itsejärjestäytyvien molekyylisysteemien rakenneosina
- Rissanen, Kari
- Suomen Akatemia
OKM-raportointi: Kyllä
Raportointivuosi: 2016
JUFO-taso: 1