Recognition of Lysine Residues on Protein Surfaces Using Calixarenes and its Application

Abstract

A macrocyclic calix[6]arene carboxylic acid derivative is found to extract lysine-rich protein cytochrome c from aqueous media into organic media through the complexation between the calixarene molecules and lysine residues on the surface of the protein. This article summarizes both the mechanism of protein extraction by the calixarene as well as the potential applications of the extraction process. The extraction process can be used for the purification of proteins through selective extraction and back-extraction under optimized conditions. On the other hand, the extracted protein exhibits enzymatic activity in organic media. The formation of a supramolecular complex by recognizing the residues on a protein surface can be construed as a novel recognition and/or modification method for biomacromolecules.

Recognition of exterior protein surfaces using artificial ligands based on calixarenes, crown ethers, and tetraphenylporphyrins

“…Some residues can be targeted for specific complexation with synthetic ligands. For example, 18-crown-6 and calix [6]arene derivatives act as a host for the e-amino group of the lysine residue, which is included into the host cavity [11][12][13][14][15][16][17]. Coordination between the imidazole group of histidine residues and transition metal ions such as Cu(II), Ni(II), Co(II), and Zn(II) can be used as a specific interaction in immobilized metal affinity chromatography [18][19][20][21].…”

“…However, there have been a number of recent studies on complexation of calixarene-based artificial receptors and biomacromolecules [36]. Some calixarene derivatives are able to bind protein amino acid residues in a similar manner to smaller amino acids and peptides [12,37]. Other calixarene derivatives possess multivalent functionalities for complexation with whole proteins [13].…”

Enhanced Extraction of Amino Compounds Using Dicyclohexyl-18-crown-6 as a Ligand in an Aqueous Two-phase System

“…18-crown-6 is well-known as a receptor entrapping amino compounds due to its suitably sized cavity for the inclusion of protonated amino groups (-NH 3 + ) [15][16][17][18]. In a similar manner, 18-crown-6 recognizes also the protonated primary amino groups of a protein, resulting in the formation of a supramolecular complex between the crown ether molecules and the protein [19][20][21][22]. Recently, extraction of a cationic protein cytochrome c into an ionic liquid using a crown ether as the extractant has been accomplished [23,24].…”

Adsorption of amino acid derivatives on calixarene carboxylic acid impregnated resins

“…A variety of calixarene derivatives has been developed in the past few decades for molecular recognition of biomolecules [1][2][3][4][5][6]. The rigid macrocyclic structure of calixarene is versatile as a platform for designing a receptor that binds to a biomolecule via multiple interactions.…”

“…In particular, various calixarene derivatives have been developed for the recognition of amino compounds. A calix [6]arene carboxylic acid derivative (abbreviated as t Oct [6]CH 2 COOH, whose structure is shown in Fig. 1) has been found to act as a host molecule for the extraction of amino acids.…”