95634-16-5Relevant academic research and scientific papers
Syntheses of Macrocyclic Enzyme Models. Part 6. Preparation and Guest-Binding Behaviour of Octopus Cyclophanes
Murakami, Yukito,Kikuchi, Jun-ichi,Suzuki, Masashi,Matsuura, Takeo
, p. 1289 - 1300 (2007/10/02)
The following octopus cyclophanes constructed with a rigid macrocyclic skeleton and eight flexible hydrocarbon chains were prepared: N,N',N'',N'''-tetrakis(2-carbamoyl>ethyl)-3,10,21,28-tetraoxo-2,11,20,29-tetra-azaparacyclophane tetrachloride 2Lys2C14)4> and N,N',N'',N'''-tetrakispentan-5-yl>carbamoyl)ethyl>-3,10,21,28-tetraoxo-2,11,20,29-tetra-azaparacyclophane tetrabromide 2Lys(C5N+)2C14>4>.These host molecules provide cavities that are deep and hydrophobic enough to incorporate hydrophobic guests of various bulkiness through an induced-fit mechanism originating from the flexible character of the alkyl branhes.Both hydrophobic and electrostatic interactions come into effect in the host-guest complexation process, so that the molecular recognition is excercised by the preset hosts toward guests molecules.As regards the inclusion equilibrium between APC2Lys(C5N+)2C14>4 and pyrene, formation of both 1:2 and 1:1 (host:guest) complexes was remarkably favoured.The hydrophobic cage provided by the octopus cyclophane is highly apolar and acts to repress the molecular motion of guests; this was confirmed by fluorescene and fluorescence polarization spectroscopy, respectively.Both 2-azidobiphenyl and pyrene were simultaneously incorporated into the cyclophane cage as evidenced by kinetic analysis, and the pyrene-senzitized photolysis of the former species was enhanced under such conditions.The results imply that the octopus cyclophanes can be utilized as effective apoenzyme models for simulation of enzymatic functions.
PREPARATION AND CHARACTERIZATION OF AN OCTOPUS AZAPARACYCLOPHANE AS A HOST FOR VARIOUS HYDROPHOBIC GUEST MOLECULES
Murakami, Yukito,Kikuchi, Jun-ichi,Suzuki, Masashi,Takaki, Toshihiko
, p. 2139 - 2142 (2007/10/02)
An octopus azaparacyclophane bearing eight hydrophobic chains, N,N',N'',N'''-tetrakiscarbamoyl>ethyl>-3,10,21,28-tetraoxo-2,11,20,29-tetraazaparacyclophane tetrachloride , was prepared and its substrate-binding behavior was examined in comparison with that of related azaparacyclophanes.
