A tight 1:1 complex between an allosteric receptor and an organic effector with hydrogen and coordination bonds. Issue 36 (7th September 2016)

• Record Type: Journal Article
• Authors: Sasaki, Yoshito; Suzuki, Shuichi; Okada, Keiji; Kozaki, Masatoshi
• Is Part Of: Tetrahedron letters. Volume 57:Issue 36(2016)
• Page Start: 4082
• Page End: 4085
• Publication Date: 2016-09-07
• Subjects: Allosteric receptor -- Porphyrin -- Hydrogen bonds -- Supramolecule -- Binding constants; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.07.088
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: An allosteric receptor and an organic effector were prepared. A receptor and an effector formed a complex with coordination and hydrogen bonds. The two binding sites were independently monitored at the same time. The degree of allosteric suppression was evaluated by UV–vis titrations. Ligand accessibility to the zinc porphyrin was restrained by allosteric mechanism. Abstract: An allosteric system1 was constructed by introducing a linear conjugated chain at position 1 and two side chains at positions 2 and 6 on the benzene ring. The conjugated chain consists of a zinc diethynyldiphenylporphyrin center (ZnDEDPP) extended to a diamidopyridine terminal. The side arm has a zinc tetraphenylporphyrin terminal (ZnTPP) linked by flexible ethylenedioxy groups. The organic effector2, possessing a uracil and two pyridine units, formed a tight 1:1 supramolecular complex with1 . The binding constant of ZnDEDPP in1 with 4-phenylpyridine was 4.2 times larger than that of ZnDEDPP in1 ·2, indicating that compound2 functions as an allosteric effector for the complexation of1 and 4-phenylpyridine.