TY - JOUR
T1 - Crystal structure of pyrogallol[4]arene complex with phosphocholine
T2 - A molecular recognition model for phosphocholine through cation-π interaction
AU - Fujisawa, Ikuhide
AU - Kitamura, Yuji
AU - Okamoto, Rumi
AU - Murayama, Kazutaka
AU - Kato, Ryo
AU - Aoki, Katsuyuki
PY - 2013/4/24
Y1 - 2013/4/24
N2 - Single crystal X-ray analysis of the complex formed between pyrogallo[4]arene (1) and phosphocholine (PCh), [Ca(H2O) 3(1)2]·(PCh-) 2·2EtOH·5H2O, a model compound that mimics PCh-receptor recognition in biological systems, has shown that PCh is incorporated into the bowl-shaped cavity of 1 through cation-π interactions between the quaternary cationic trimethylammonium group of PCh and π-rings of 1. The hepta-coordinated [Ca(H2O)3]2+ ion is directly bound to two molecules of 1 through phenolic oxygens to form a dimeric molecule of 1, [1{Ca(H2O)3}1]2+. Conformational data of PCh and its derivatives observed in known crystal structures are compiled, focusing on the conformation about the C-C bond in the P-O-C-C-N + backbone with a reemphasis that the usually observed gauche conformation could be stabilized by an intramolecular N+-C(methyl group)-H⋯O hydrogen bonding.
AB - Single crystal X-ray analysis of the complex formed between pyrogallo[4]arene (1) and phosphocholine (PCh), [Ca(H2O) 3(1)2]·(PCh-) 2·2EtOH·5H2O, a model compound that mimics PCh-receptor recognition in biological systems, has shown that PCh is incorporated into the bowl-shaped cavity of 1 through cation-π interactions between the quaternary cationic trimethylammonium group of PCh and π-rings of 1. The hepta-coordinated [Ca(H2O)3]2+ ion is directly bound to two molecules of 1 through phenolic oxygens to form a dimeric molecule of 1, [1{Ca(H2O)3}1]2+. Conformational data of PCh and its derivatives observed in known crystal structures are compiled, focusing on the conformation about the C-C bond in the P-O-C-C-N + backbone with a reemphasis that the usually observed gauche conformation could be stabilized by an intramolecular N+-C(methyl group)-H⋯O hydrogen bonding.
KW - Ca
KW - Cation-π interaction
KW - Crystal structure
KW - Molecular recognition
KW - Phosphocholine
KW - Pyrogallol[4]arene
UR - http://www.scopus.com/inward/record.url?scp=84874085902&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84874085902&partnerID=8YFLogxK
U2 - 10.1016/j.molstruc.2013.01.030
DO - 10.1016/j.molstruc.2013.01.030
M3 - Article
AN - SCOPUS:84874085902
SN - 0022-2860
VL - 1038
SP - 188
EP - 193
JO - Journal of Molecular Structure
JF - Journal of Molecular Structure
ER -