Gold compact disc appended Tröger’s base scaffolds as MALDI-TOF biodetection probes

Tröger’s base was discovered in 1887 by J. Tröger and has a V-shaped structure with C2 symmetry containing a chiral, hydrophobic cleft creating an angle of 90˚. For many years its chiral cleft has been utilised for the stationary phase of chiral HPLC columns, a chiral resolving agent and as a chiral catalyst. Over the past 30 years it has been reported that this interesting molecule can intercalate DNA, inhibit enzyme activity and behave as a synthetic receptor. The biological activity of the analogues of Tröger’s base has only been narrowly investigated. This investigation has generated a plethora of biologically interesting Tröger’s base derivatives via utilisation of ‘click’ chemistry on a novel bis-azido Töger’s base scaffold. The detection of proteins quickly, efficiently and cheaply is a huge challenge and this project aims to use cheap, readily available gold compact discs as a novel platform for the portable detection and sensing of biological interactions on the gold CD surface. The use of a gold compact disc and its ability to bind self assembled monolayers will be investigated and the detection of these biological interactions via MALDI-TOF spectrometry will be probed. The (+)-biotin / streptavidin interaction will be used as a model study for these purposes with the ambition to develop this further with humanitarian and military applications. The V-shape and 90˚ angle of Tröger’s base will be exploited to investigate its use as a scaffold for binding to gold compact discs for the development of surface based biological assays and proteomics. The incorporation of stable isotopes into organic molecules will also be investigated and we report a new protocol for the mild and efficient deuteration of terminal alkynes and their subsequent use in organic chemistry.

Name dc:type.qualificationname

phd

Level dc:type.qualificationlevel

doctoral

Grantor dc:publisher.institution

University of East Anglia

Year dc:date.issued

2013

Author dc:creator

• Hiatt-Gipson, Glyn

Language dc:language

en