Bioorganic Chemistry 2010-10-01

The binding site of zinc and indium metal to amino acid derivatized squarate complexes - Implications in inhibitor and mediator designs.

Natasha Ramroop-Singh, Dyer Narinesingh, Gurdial Singh, Christopher T Seto, Anthony B Comeau

Index: Bioorg. Chem. 38(5) , 234-41, (2010)

Full Text: HTML

Abstract

Three novel metal squaric acid-peptide complexes, SQI-SQIII were prepared by addition of indium triflate or zinc chloride to the previously reported compounds [1], 3-(hydroxymethylamino)-4-(l-isoleucine methyl ester)-3-cyclobutene-1,2-dione (squarate 1), and 3-(hydroxymethylamino)-2-(l-isoleucine methyl ester)-4-thioxo-2-cyclobuten-1-one (squarate 2). The structures of SQI-SQIII were elucidated using NMR analysis. The electrochemical applications of two of these metal-squaric acid systems (SQI and SQII) were also investigated. Incorporation of SQII as a mediator, in the previously optimized Pt/p(HEMA)/p(pyrrole)/GOx electrode using the ionic liquid [bmim][BF(4)] as the solvent medium, produced a biosensor with enhanced properties, namely a sensitivity of 175.9mA/M d-glucose, working potential of +200mV, large linear range (0-12mM) and a detection limit of 1x10(-6)M.2010 Elsevier Inc. All rights reserved.