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Solution-Based Molecular Recognition



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University of Missouri Columbia Department of Chemistry Organic Cume May 5 2007 Dr Rainer Glaser Solution Based Molecular Recognition Leading Reference Differential receptor arrays and assays for solution based molecular recognition Wright A T Anslyn E V Chem Soc Rev 2006 35 14 28 1 Question 1 Differential Sensor Arrays Arrays of derivatized beads are created to simultaneously identify multiple analytes 20 points a The beads are derivatized with sensor molecules and two sensor molecules are listed below Briefly state what the each molecule senses and how this sensing is accomplished big picture responses suffice 8 points Fluorescein Boronic ester b Differential sensor arrays employ CCDs for the analysis Explain what CCD stands for and what a CCD does i e what data are measured 6 points CCD stands for What a CCD measures c Differential sensor arrays can be used to perform indicator displacement assays IDA Briefly explain the idea of the IDA and feel free to exemplify if you wish 6 points 2 Question 2 Molecular Imprinting 20 points From the review As an initial demonstration of MIPs within sensor arrays Mirsky used a simple spreader bar approach for the development of differential sensors In this case thiol modified purines and pyrimidines spreader bar molecules were coadsorbed onto a gold surface with dodecanethiol matrix molecule Self assembled monolayers SAMs formed having significant differential reactivity towards a number of nucleic acids adenine cytosine thymine uracil caffeine and uric acid The primary detection method was measurement of the capacitive current Five different spreader bar molecules were employed in the development of the array 6 mercaptopurine ASH 2 amino 6purinethiol GSH 4 amino 2 mercaptopyrimidine CSH 4 hydroxy 5 methyl 2 mercaptopyrimidine TSH 4 hydroxy 2 mercaptopyrimidine USH a Draw two of the spreader bar molecules employed in the array 6 points b Draw a cartoon of a SAM that contains one type of spreader bar molecule 8 points c Explain what is being measured in the analysis that is explain the sentence The primary detection method was measurement of the capacitive current 6 points 3 Question 3 Porphyrin Fluorescent Surface Protein Receptors 20 points From the review Hamilton has created a sensor array for the detection of multiple proteins using tetraphenylporphyrins TPP These porphyrins have large hydro phobic surface areas that are excellent for protein recognition Derivatization of the TPP periphery with various resulted in a library with receptors encompassing differing charges size hydrophobicity and symmetry well suited to the recognition of proteins with various surface characteristics The TPP derivatives also are highly fluorescent making signal detection and pattern development facile a About the blank What kinds of molecules are used to derivatize the TPP periphery 4 points b Using concepts and terminology of intermolecular bonding explain the statement porphyrins have large hydrophobic surface areas and state how this property is used in protein recognition 8 points c The measurement is based on fluorescence quenching What is being measured for which chromophore s and how is the measured quantity influenced by the presence of analyte 8 points 4 Question 4 Microtiter Plate Arrays 20 points Sometimes the quantitative measurement is not linear with analyte concentration In such cases one can resort to so called traffic light signalling systems Fig 12 shows such an application based on the measurement of the fluorescence and the phosphorescence of indicators dispersed in water soluble thin films of poly ethylene glycol on the bottom of MTP wells Explain how the determination is made as to whether any given well is green or red Do the colors green and red have anything to do with the indicator s color and if so what is that connection Concept knowledge is sought quantitative knowledge is not expected 5 Question 5 Synthetic Biomolecule Assays 20 points From the Review adapted An example of synthetic biomolecules in arrays was completed by Basu In this study two liposomes were prepared by polymerization of 22 95 mol and either 23 or 24 5 mol These liposomes change color from red to blue when bound to an analyte Using this rather simple two sensor array lipopolysaccharides LPS from various Gram negative bacteria were discriminated a Draw any trimer formed by trimerization of two molecules 22 and one molecule 23 10 points b Draw a cartoon of the liposome formed by the co polymer of 22 and 23 Draw the cartoon any way you like Anything that makes sense and described the essential architecture of the liposome will receive credit 10 points 6


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